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Chemical Structure| 14963-97-4
Chemical Structure| 14963-97-4
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Product Details of [ 14963-97-4 ]

CAS No. :14963-97-4 MDL No. :MFCD17014918
Formula : C9H8O5 Boiling Point : -
Linear Structure Formula :- InChI Key :DULQZGQVLHMCAU-UHFFFAOYSA-N
M.W : 196.16 Pubchem ID :315218
Synonyms :

Calculated chemistry of [ 14963-97-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.85
TPSA : 83.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.88
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 0.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.98
Solubility : 2.08 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (Ali) : -2.63
Solubility : 0.46 mg/ml ; 0.00235 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.28
Solubility : 10.4 mg/ml ; 0.0528 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 14963-97-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14963-97-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14963-97-4 ]

[ 14963-97-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 908094-01-9 ]
  • [ 14963-97-4 ]
  • [ 32136-52-0 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; ethanol
  • 2
  • [ 2944-49-2 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
76.75% With potassium permanganate; cetyltrimethylammonim bromide; In N,N-dimethyl-formamide; at 70 - 90℃; for 4.5h; A 500 mL three-necked flask was charged with 100.00 g of DMF, 27.24 g (0.20 mol) of <strong>[2944-49-2]1-methoxy-2,3-dimethylbenzene</strong>,And cetyltrimethylammonium bromide 14.58g (0.04mol), warmed to 70 C, began to part-time potassium permanganate 79.01g (0.50mol), the temperature does not exceed 90 , about 30min plus finished,After adding insulation 80 ~ 90 reaction 4h,Cooled to room temperature, 300g of water was added dropwise, filtered and washed with water 100.00g * 3 to give a white solid, dried at 55-60 C, the theoretical 39.23g,Yield 76.75%, purity 98.70%.
75% With potassium permanganate; In tert-butyl alcohol; for 0.5h;Reflux; 2) 2,3-Dimethyl anisole is dissolved in tert-butyl alcohol. Under reflux, potassium permanganate solution is added dropwise until dissolved.After the liquid color remains reddish for 30 minutes, add a little sodium sulfite to remove excess potassium permanganate, filter, and extract with ethyl acetate.Taken, the extract was distilled off to give 3-methoxyphthalic acid in a yield of 75%.
  • 3
  • [ 14963-97-4 ]
  • [ 14963-96-3 ]
YieldReaction ConditionsOperation in experiment
100% With acetic anhydride In tetrahydrofuran at 80℃; for 3h; 11 [0228] To a solution of 3-methoxyphthalic acid (3.0 g, 15.306 mmol) in THF (24 mL) at RT was added acetic anhydride (10 mL). The mixture was stirred at 80 oC for 3 hrs. The solvent was evaporated to give 4-methoxyisobenzofuran-1,3-dione (2.72 g, quant. yield) as a white solid. MS (ESI) m/z = 178.9 [M+H]+.
99% With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; 56.56A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1 H, d), 4.02 (3H, s). MS: [M+H]+ 179.
99% With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mo.) [prepared as per J. Chem, Soc,Perkin Trans. 7, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179.A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSOd6) 11.08 (1 H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1 H1 d), 3.93 (3H, s). MS: [M+Hf 178.A stirred solution of 3-methoxyphthalimide (8.95 g, 50.56 mmol) in anhydrous tetrahydrofuran (200 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 150 ml, 0.15 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (60 ml) was added dropwise followed by 5M hydrochloric acid (60 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the mixture diluted with water (250 ml) and extracted with dichloromethane (3 x 250 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 250 ml) and the combined extracts were evaporated to dryness in vacuo to afford 4-methoxyisoindoline (4.44 g, 59%) as a green oil which was used without further purification. 1H NMR (DMSO-d6) 7.18 (1H, t), 6.83 (1 H, d), 6.78 (1 H, d), 4.07 (2H1 s), 4.02 (2H, s), 3.78 (3H, s). MS: [M+H]+ 150.4-Methoxyisoindoline (4.4 g, 29.53 mmol) in 48% aqueous hydrobromic acid (50 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-hydroxyisoindoline hydrobromide (5.0 g, 78%) as a pale orange solid. 1H NMR (DMSO-d6) 9.95 (1 H, br s), 9.37 (2H, br s), 7.19 (1 H, t), 6.84 (1 H, d), 6.80 (1H, d), 4.48 (2H, t), 4.40 (2H, t). MS: [M+Hf 136.
99% With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; 56.A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1 H, dd), 7.63 (1H1 d), 7.60 (1 H1 d), 4.02 (3H, s). MS: [M+H]+ 179.
99% With acetic anhydride In tetrahydrofuran for 4h; Reflux; 56.A 56A. Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was stirred and held at reflux for 4 hours.Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 50° C. overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1H, dd), 7.63 (1H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179.
97.8% With acetic anhydride In tetrahydrofuran at 20 - 80℃; for 4h; (S)-2-((2-(2,7-Dioxoazepan-3-yl)- 1 ,3-dioxoisoindolin-4-yl)oxy)-N-(6-(2-((1 -(4-(3-oxo-9- phenyl-2,3 -dihydro- [1 ,2,4ltriazolo[3 ,4-fl [1 ,6lnaphthyridin-8-yl)phenyl)cyclobutyl)amino)acetamido)hexyl)acetamide (Compound 73) [0582] To a solution of 3-methoxyphthalic acid (3.0 g, 15.3 mmol) in THF (30 mL) at rt was added acetic anhydride (10 mL) and the reaction was heated at 80°C for 4 hrs. The solvent was removed and the residue was dried under vacuum providing 4- methoxyisobenzofuran-1,3-dione (2.66 g, 97.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.98-7.94 (m, 1H), 7.63-7.59 (m, 2H), 4.01 (s, 3H).
95% at 200℃;
94% With acetic anhydride Reflux; 1.3 3) 3-methoxy-phthalic acid plus 2 times the weight of acetic anhydride, after heating and refluxing, cooling and crystallization,The 3-methoxy-phthalic anhydride is filtered,Yield 94%.
at 170℃; Erhitzen unter vermindertem Druck;
With acetic anhydride; acetyl chloride
With acetic anhydride
With acetic anhydride for 1h; Heating;
With acetic anhydride Heating;
With acetyl chloride for 6h; Yield given;
Multi-step reaction with 2 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C
With acetic anhydride In tetrahydrofuran for 4h; Reflux; 3.1.1. General Procedure for Synthesis of 4-Methoxy-2-benzofuran-1,3-dione (2) The 4-methoxy-2-benzofuran-1,3-dione was obtained from1, according to a previously published procedure [32], with slight modifications. Briefly, 2,3-dimethylphenyl methyl ether (3.4 g, 25 mmol) was dissolved in water (98 mL) and tert-butanol (42 mL). After potassium permanganate (25 g, 160 mmol) was added, the reaction mixture was refluxed for 12 h. The resulting suspension was filtered over Celite, concentrated to 50 mL, acidified with 37% hydrochloric acid, and left standing overnight at room temperature. The 3-methoxybenzene-1,2-dicarboxylic acid crystallized as a white solid (4.34 g) and was refluxed for 4 h in anhydrous tetrahydrofuran (24 mL) with the addition of acetic anhydride (7 mL). Upon cooling to room temperature, the reaction mixture was concentrated in vacuo and the white solid was dried at 50 °C for 48 h, to afford 4-methoxy-2-benzofuran-1,3-dione (3.82, 97%). HPLC:Rt= 0.931, MS calcd for [M + H]+: C9H6O4m/z: 178.14, found: 178.97;1H-NMR (300 MHz, DMSO-d6) δ ppm 3.99 (s, 3 H) 7.59 (dd,J= 9.67, 7.91 Hz, 2 H) 7.90-7.97 (m, 1 H).

Reference: [1]Current Patent Assignee: BIOTHERYX INC - WO2019/40274, 2019, A1 Location in patent: Paragraph 0228
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2008/44029, 2008, A1 Location in patent: Page/Page column 245
[3]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2008/44041, 2008, A1 Location in patent: Page/Page column 267-268
[4]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2008/44045, 2008, A1 Location in patent: Page/Page column 319-320
[5]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - US2010/152184, 2010, A1 Location in patent: Page/Page column 103
[6]Current Patent Assignee: BIOTHERYX INC - WO2017/201069, 2017, A1 Location in patent: Paragraph 0582
[7]Gupta, Dahmendra N.; Hodge, Philip; Hurley, Peter N. [Journal of the Chemical Society. Perkin transactions I, 1989, p. 391 - 394]
[8]Current Patent Assignee: SANWEI INDUSTRIAL TECH RESEARCH INSTITUTE OF CHANG - CN107698442, 2018, A Location in patent: Paragraph 0019; 0022; 0024
[9]Blair et al. [Journal of the Chemical Society, 1955, p. 708,711] Girardet [Helvetica Chimica Acta, 1931, vol. 14, p. 4511]
[10]Asahina; Asano [Chemische Berichte, 1930, vol. 63, p. 2059,2062][Yakugaku Zasshi, 1930, vol. 50, p. 1103,1107, 1108]
[11]Leffler; Graybill [Journal of Physical Chemistry, 1959, vol. 63, p. 1457,1460]
[12]Soucy; Favreau; Kayser [Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 129 - 134]
[13]Makhlouf, Mansour A.; Rickborn, Bruce [Journal of Organic Chemistry, 1981, vol. 46, # 23, p. 4810 - 4811]
[14]De Silva; Reed; Billedeau; Wang; Norris; Snieckus [Tetrahedron, 1992, vol. 48, # 23, p. 4863 - 4878]
[15]Gupta, Dahmendra N.; Hodge, Philip; Hurley, Peter N. [Journal of the Chemical Society. Perkin transactions I, 1989, p. 391 - 394]
[16]Czopek, Anna; Partyka, Anna; Bucki, Adam; Pawłowski, Maciej; Kołaczkowski, Marcin; Siwek, Agata; Głuch-Lutwin, Monika; Koczurkiewicz, Paulina; Pękala, Elżbieta; Jaromin, Anna; Tyliszczak, Bożena; Wesołowska, Anna; Zagórska, Agnieszka [Molecules, 2020, vol. 25, # 17]
  • 4
  • [ 14963-97-4 ]
  • [ 601-97-8 ]
YieldReaction ConditionsOperation in experiment
91.98% With boron tribromide In dichloromethane at 10 - 15℃; for 5h; 6 A 500 mL three-necked flask was charged with 150.00 g of methylene chloride and 30.00 g of 3-methoxyphthalic acid(0.15mol), water bath temperature 10 ~ 15 ° C was added dropwise boron tribromide 95.22g (0.38mol), after the addition was completed, the reaction was continued heat5h. In another 1000mL three-necked flask was added 450.00g ice water mixture, the above reaction solution was slowly poured into ice water, controlTemperature does not exceed 30 ° C, and then continue stirring for 1h, filtered, washed with water to pH = 6, 55 ~ 60 dried to give a white solid, theory27.79g,Real 25.56g, yield 91.98%, purity 99.23%.
With potassium carbonate beim Schmelzen;
  • 5
  • [ 32136-52-0 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
99% With potassium hydroxide In ethanol; water
99% With potassium hydroxide In ethanol; water other reagents and solvents at various temperatures;
84% Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water 56.56A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc,Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSOd6) 13.05 (2H1 br s), 7.48 (2H, m), 7.33 (1 H, m), 3.82 (3H, s). MS: [M+H]+ 197.
84% Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mo.) [prepared as per J. Chem, Soc,Perkin Trans. 7, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179.A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSOd6) 11.08 (1 H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1 H1 d), 3.93 (3H, s). MS: [M+Hf 178.A stirred solution of 3-methoxyphthalimide (8.95 g, 50.56 mmol) in anhydrous tetrahydrofuran (200 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 150 ml, 0.15 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (60 ml) was added dropwise followed by 5M hydrochloric acid (60 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the mixture diluted with water (250 ml) and extracted with dichloromethane (3 x 250 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 250 ml) and the combined extracts were evaporated to dryness in vacuo to afford 4-methoxyisoindoline (4.44 g, 59%) as a green oil which was used without further purification. 1H NMR (DMSO-d6) 7.18 (1H, t), 6.83 (1 H, d), 6.78 (1 H, d), 4.07 (2H1 s), 4.02 (2H, s), 3.78 (3H, s). MS: [M+H]+ 150.4-Methoxyisoindoline (4.4 g, 29.53 mmol) in 48% aqueous hydrobromic acid (50 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-hydroxyisoindoline hydrobromide (5.0 g, 78%) as a pale orange solid. 1H NMR (DMSO-d6) 9.95 (1 H, br s), 9.37 (2H, br s), 7.19 (1 H, t), 6.84 (1 H, d), 6.80 (1H, d), 4.48 (2H, t), 4.40 (2H, t). MS: [M+Hf 136.
84% Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc,Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSOd6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.
84% Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water 56.56A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc, Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+Hf 197.
84% With water; potassium hydroxide for 4h; Reflux; 56.A 56A. A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc., Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 50° C. overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.
Hydrolysis;
hydrolysis;

  • 7
  • [ 17802-94-7 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate; sulfuric acid at 0℃;
  • 8
  • [ 19056-23-6 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In ethanol
  • 9
  • [ 67-56-1 ]
  • [ 14963-97-4 ]
  • [ 60314-07-0 ]
YieldReaction ConditionsOperation in experiment
65% With Amberlyst 15 beads for 48h; Heating;
  • 10
  • [ 4792-33-0 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide; potassium permanganate In water for 12h; Ambient temperature;
  • 11
  • [ 1008-19-1 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
71.55% With potassium permanganate; cetyltrimethylammonim bromide In dimethyl sulfoxide at 75 - 90℃; for 3.16667h; 3 To a 1000 mL three-necked flask, 120.0 g of DMSO, 32.45 g of 5-methoxy-1,2,3,4-tetrahydronaphthalene(0.20 mol) and cetyltrimethylammonium bromide 36.44g (0.10mol), warmed to 75 ° C, the beginning of the partial addition of permanganic acidPotassium 110.62g (0.70mol), temperature control does not exceed 90 , about 40min plus finished, after adding insulation 80 ~ 90 reaction 2.5h, coolingTo room temperature, dropping 600g of water, filtration, water 100.00g * 3 washed, to give a white solid, 55 ~ 60 drying theory 39.23g,Real 28.07g, yield 71.55%, purity 98.41%.
65% With potassium permanganate; cetyltrimethylammonim bromide In water; benzene for 2h; Heating;
  • 12
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  • [ 90047-52-2 ]
YieldReaction ConditionsOperation in experiment
71% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;
20% Stage #1: 3-methoxyphthalic acid With dimethylsulfide borane complex In tetrahydrofuran at -6 - 55℃; Stage #2: With sodium hydroxide In tetrahydrofuran at 20℃; for 1h;
With sodium hydroxide In tetrahydrofuran; water 5 EXAMPLE 5 EXAMPLE 5 A solution of 3-methoxyphthalic acid (19.6 g, 0.1 mol) in 100 ml of tetrahydrofuran was added to 10 g (0.263 mol) of lithium aluminum hydride in 500 ml of anhydrous ether at a rate sufficient to maintain a constant reflux. The mixture was refluxed for 2 hours after the addition was completed. It was cooled and decomposed by the addition of 10 ml of water, 20 ml of 10% sodium hydroxide and 40 ml of water. The resulting solid was separated by filtration and washed with tetrahydrofuran. The combined filtrates were concentrated to give 12 g of 3-methoxy-o-xylene-α,α'-diol; m.p. 95°.
  • 13
  • [ 72049-14-0 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; potassium permanganate In water Heating;
  • 14
  • [ 83650-24-2 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide In ethanol; water for 2h; Heating;
  • 15
  • [ 14963-97-4 ]
  • [ 100-36-7 ]
  • [ 77763-85-0 ]
YieldReaction ConditionsOperation in experiment
70% at 170℃; for 1h;
  • 16
  • [ 4938-06-1 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
61% With potassium permanganate
  • 17
  • [ 10075-63-5 ]
  • permanganate [ No CAS ]
  • [ 14963-97-4 ]
  • 18
  • [ 14963-97-4 ]
  • 3-methoxy-N-hydroxyphthalimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With hydroxylamine hydrochloride at 170℃; for 5h;
  • 19
  • [ 526-75-0 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / tetabutylammonium hydrogensulfate; K2CO3 / acetone / 24 h / Heating 2: 40 percent / KMnO4 / 2-methyl-propan-2-ol; H2O / 2 h / Heating
Multi-step reaction with 2 steps 1: NaOH-solution 2: potassium permanganate
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 2 h / 10 - 50 °C 2: potassium permanganate / <i>tert</i>-butyl alcohol / 0.5 h / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 75 °C 2: potassium permanganate / water; <i>tert</i>-butyl alcohol / 12 h / Reflux

  • 20
  • [ 14963-97-4 ]
  • (+/-)-2-amino-4-hydroxyindane-2-phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating 6.1: BBr3 / CH2Cl2 / 0 °C 7.1: aq. hydrochloric acid / 20 h / Heating
  • 21
  • [ 14963-97-4 ]
  • [ 932745-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating
  • 22
  • [ 14963-97-4 ]
  • [ 932745-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C
  • 23
  • [ 14963-97-4 ]
  • (2-benzyloxycarbonylamino-4-hydroxy-indan-2-yl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating 6.1: BBr3 / CH2Cl2 / 0 °C
  • 24
  • [ 14963-97-4 ]
  • [ 932745-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating
  • 25
  • [ 14963-97-4 ]
  • [ 71785-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating
  • 26
  • [ 14963-97-4 ]
  • [ 4792-33-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / Heating 2: L-Selectride / tetrahydrofuran / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: acetic anhydride / 1 h / Heating 2: LiBH4 / tetrahydrofuran / 2 h / -10 - 20 °C / other 3-substituted phthalic anhydrides; var. reducing agents and reaction conditions
Multi-step reaction with 2 steps 1: 170 °C / Erhitzen unter vermindertem Druck 2: acetic acid; aqueous hydrochloric acid; zinc
  • 27
  • [ 14963-97-4 ]
  • [ 28281-58-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / Heating 2: L-Selectride / tetrahydrofuran / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: acetic anhydride / 1 h / Heating 2: LiBH4 / tetrahydrofuran / 2 h / -10 - 20 °C / other 3-substituted phthalic anhydrides; var. reducing agents and reaction conditions
Multi-step reaction with 2 steps 1: 170 °C / Erhitzen unter vermindertem Druck 2: acetic acid; aqueous hydrochloric acid; zinc
  • 28
  • [ 14963-97-4 ]
  • [ 90047-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C
  • 29
  • [ 14963-97-4 ]
  • [ 90047-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature
  • 30
  • [ 14963-97-4 ]
  • [ 90047-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2
  • 31
  • [ 14963-97-4 ]
  • [ 90047-55-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C
  • 32
  • [ 14963-97-4 ]
  • [ 90047-56-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C 8: 0.4 g / K2CO3 / acetone / 8 h / Heating
  • 33
  • [ 14963-97-4 ]
  • [ 90047-54-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature
  • 34
  • [ 14963-97-4 ]
  • [ 90047-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating
  • 35
  • [ 14963-97-4 ]
  • [ 90047-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C 8: 0.4 g / K2CO3 / acetone / 8 h / Heating 9: LiAlH4 / diethyl ether / 5 h / Heating
  • 36
  • [ 14963-97-4 ]
  • [ 77763-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 70 percent / 1 h / 170 °C 2: hydrochloric acid / methanol
  • 37
  • [ 2216-69-5 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / Raney-nickel / ethanol / 150 °C / 91200.1 - 114000 Torr 2: 65 percent / KMnO4 / cetyltrimethylammonium bromide / benzene; H2O / 2 h / Heating
  • 38
  • [ 481-72-1 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H3BO3 / 6 h / Heating 2: Ag2O / dimethylformamide 3: KMnO4, KOH / H2O / Heating
  • 39
  • [ 72049-18-4 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 12 h / Heating 2: KMnO4, KOH / H2O / Heating
Multi-step reaction with 2 steps 1: Ag2O / dimethylformamide 2: KMnO4, KOH / H2O / Heating
  • 40
  • [ 72049-19-5 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Ag2O / dimethylformamide 2: KMnO4, KOH / H2O / Heating
  • 41
  • [ 72049-16-2 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 mg / HCl(aq.) / methanol; H2O / 3 h / Heating 2: KMnO4, KOH / H2O / Heating
  • 42
  • [ 14963-97-4 ]
  • [ 121364-89-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C 3: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C 4: 343 mg / triethylsilane / trifluoroacetic acid / 18 h
Multi-step reaction with 3 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: 1.) thionyl chloride, 2.) stannic chloride, 3.) 10percent aq. KOH 3: 343 mg / triethylsilane / trifluoroacetic acid / 18 h
Multi-step reaction with 3 steps 1: 95 percent / 200 °C 2: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C 3: 343 mg / triethylsilane / trifluoroacetic acid / 18 h
  • 43
  • [ 14963-97-4 ]
  • [ 121364-88-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C 3: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C
Multi-step reaction with 2 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: 1.) thionyl chloride, 2.) stannic chloride, 3.) 10percent aq. KOH
Multi-step reaction with 2 steps 1: 95 percent / 200 °C 2: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C
  • 44
  • [ 53005-44-0 ]
  • [ 14963-97-4 ]
  • 45
  • [ 14963-97-4 ]
  • [ 37418-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potash / beim Schmelzen 2: 150 °C
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 2: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C
  • 46
  • [ 52289-93-7 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetonitrile 2: NaNH2, liq. NH3 3: aq. NaOH, KMnO4 4: aq. NaOH, KMnO4
  • 47
  • Pillaromycinone, <3(S),4(R),4a(R),12a(R)>-2-Acetyl-3,4,4a,5,12,12a-hexahydro-12-oxo-3,4,10,11,12a-pentahydroxy-naphthacene [ No CAS ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: KMnO4, aq. NaOH
  • 48
  • [ 14963-97-4 ]
  • [ 60314-07-0 ]
YieldReaction ConditionsOperation in experiment
63% With hydrogenchloride In methanol; water-methanol 6 Preparation of Methoxyphthalic Acid Monomethylester [derivative of formula (VIII) in which R2 =R3 =CH3 ] EXAMPLE 6 Preparation of Methoxyphthalic Acid Monomethylester [derivative of formula (VIII) in which R2 =R3 =CH3 ] A solution of methoxyphthalic acid obtained as per Example 5 (0.1 mol) in 100 ml methanol was added with CuCl (0.1 mol) and HCl (0.1 mol). The solution was heated to reflux for 30 min. The clear solution obtained was evaporated to dryness under reduced pressure. The residue obtained was dissolved in a 1:3 water-methanol mixture and acidified. The product was separated by cooling, collected by filtration and air dried. The product yield was 63-66%.
  • 49
  • [ 14963-97-4 ]
  • [ 108-24-7 ]
  • [ 14963-96-3 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran for 4h; Heating / reflux; 56.56A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1 H, d), 4.02 (3H, s). MS: [M+H]+ 179.
  • 50
  • [ 201230-82-2 ]
  • [ 579-75-9 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
45% With sodium acetate; palladium diacetate; silver carbonate In 1,4-dioxane at 150℃; for 30h;
  • 51
  • [ 2944-49-2 ]
  • [ 14963-96-3 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,3-dimethylanisole With potassium permanganate In water; <i>tert</i>-butyl alcohol for 6h; Reflux; Stage #2: With hydrogenchloride In water; <i>tert</i>-butyl alcohol 98-2 SYNTHESIS EXAMPLE 98-2 After 2,3-dimethyl anisole (10 g) was dissolved in a mixed solvent of water (250 mL) and t-butanol (112 mL), potassium permanganate (81.2 g) was added, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, an insoluble matter was filtered with Celite, followed by washing with water. After the filtrate was acidified with concentrated hydrochloric acid and concentrated under reduced pressure, a mixture (4.9 g) of 3-methoxyphthalic anhydride and 3-methoxyphthalic acid was obtained. This mixture was heated to reflux in acetic anhydride (8.5 mL) for 2 hours. After an insoluble matter was filtered off in the hot state, the filtrate was left overnight at room temperature, and the precipitated crude crystal was washed with a t-butylmethylether/petroleum ether mixed solvent to obtain 3-methoxyphthalic anhydride (3.21 g). 1H-NMR (CDCl3, δ ppm): 4.08 (3H, s), 7.33 (1H, d), 7.58 (1H, d), 7.84 (1H, dd).
  • 52
  • [ 37418-88-5 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3.1: sodium hydroxide; water / 1,4-dioxane / 80 °C 3.2: pH 3
  • 53
  • [ 38157-42-5 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
52.9% Stage #1: diethyl 3-methoxyphthalate With water; sodium hydroxide In 1,4-dioxane at 80℃; Stage #2: With hydrogenchloride In water 4.2 3-Methoxyphthalic acid (5b) To a 1,4-dioxane (1.0 mL) solution of 4b (34.0 mg, 0.135 mmol), 5.0 mol/L NaOH solution (5.0 mL) was added. The mixture was stirred at 80°C for overnight. The reaction mixture was extracted with EtOAc three times. 1.0 mol/L HCl solution was added to the aqueous solution to adjust the until pH3, and then extracted with EtOAc three times. The organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure to give 5b (14.0 mg, 52.9%).
  • 54
  • [ 6161-63-3 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
98.32% With potassium permanganate; cetyltrimethylammonim bromide In water at 80 - 90℃; for 6.5h; 2 To 500mL three-necked flask was added 240.00g of water,1-Methoxy-2-ethyl-3-methylbenzene 30.04 g (0.20 mol)And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 80 ° C and 63.21 g of potassium permanganate(0.40mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 6h, cooled to room temperature, tooFiltered, washed with water 100.00g * 3, to give a white solid, dried at 55 ~ 60 , the theory of 39.23g, solid 32.17g, yield82.00%, purity of 98.32%.
  • 55
  • 1-methoxy-2-propyl-3-ethylbenzene [ No CAS ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
80.8% With potassium permanganate; cetyltrimethylammonim bromide In water at 70 - 90℃; for 8.5h; 4 To 500mL of three-necked flask was added 250.00g of water,1-methoxy-2-propyl-335.65 g (0.20 mol) of ethylbenzene And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 70 ° C and 63.21 g of potassium permanganate(0.41mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 8h, cooled to room temperature, tooFiltered, washed with water 100.00g * 3, to give a white solid, dried at 55 ~ 60 , the theory of 39.23g, was 31.70g, yield80.80%, purity of 98.03%.
  • 56
  • [ 21573-42-2 ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
81.98% With potassium permanganate; cetyltrimethylammonim bromide; In water; at 70 - 90℃; for 7.5h; To a 500 mL three-necked flask, 210.00 g of water and 29.64 g (0.20 mol) of <strong>[21573-42-2]<strong>[21573-42-2]4-methoxyindan</strong>e</strong> were added,And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 70 C. 79.02 g (0.50 mol) of potassium permanganate was added in portions,Temperature does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 7h, cooled to room temperature, filtered, water 100.00g * 3Washed to give a white solid, 55 ~ 60 drying theory 39.23g, in real 32.16g, yield 81.98%, purity 98.53%.
  • 57
  • 1-methoxy-2,3-dipropylbenzene [ No CAS ]
  • [ 14963-97-4 ]
YieldReaction ConditionsOperation in experiment
77.57% With potassium permanganate; cetyltrimethylammonim bromide In N,N-dimethyl-formamide at 70 - 90℃; for 4.5h; 6 To a 500 mL three-necked flask were added 100.00 g of DMF, 38.46 g (0.2 mol) of 1-methoxy-2,3-dipropylbenzene andCetyltrimethylammonium bromide 14.58g (0.04mol), warmed to 70 ° C, the initial addition of potassium permanganate 79.01g(0.50mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 4h, cooled to room temperature, dropwise300.00g of water, filtered, washed with water 100.00g * 3, to give a white solid, 55 ~ 60 drying,Theory 39.23g, in fact, 30.43g, yield 77.57%, purity 98.91%.
  • 58
  • [ 14963-97-4 ]
  • (S)-4-methoxy-2-(2-oxoazepan-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C
Multi-step reaction with 2 steps 1.1: acetic anhydride / tetrahydrofuran / 3 h / 80 °C 2.1: acetic acid / acetonitrile / 85 °C 2.2: 85 °C
  • 59
  • [ 14963-97-4 ]
  • (S)-2-(2,7-dioxoazepan-3-yl)-4-methoxyisoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C
  • 60
  • [ 14963-97-4 ]
  • (S)-2-(2,7-dioxoazepan-3-yl)-4-hydroxyisoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C
  • 61
  • [ 14963-97-4 ]
  • (S)-tert-butyl (4-(2-((2-(2,7-dioxoazepan-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamido)butyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C
  • 62
  • [ 14963-97-4 ]
  • (S)-N-(4-aminobutyl)-2-((2-(2,7-dioxoazepan-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
  • 63
  • [ 14963-97-4 ]
  • 2-((S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)-N-(4-(2-((2-((S)-2,7-dioxoazepan-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamido)butyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 7: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C
  • 64
  • [ 14963-97-4 ]
  • (S)-(R)-3-(3,4-dimethoxyphenyl)-1-(3-(4-((4-(2-((2-((S)-2,7-dioxoazepan-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetamido)butyl)amino)-4-oxobutanamido)phenyl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 7: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C
  • 65
  • [ 14963-97-4 ]
  • (S)-tert-butyl (1-((2-(2,7-dioxoazepan-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)-2-oxo-7,10,13-trioxa-3-azahexadecan-16-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C
  • 66
  • [ 14963-97-4 ]
  • [ 21794-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 °C 3: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 - 20 °C 3: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 2.2: 0 - 20 °C 3.1: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere
  • 67
  • [ 14963-97-4 ]
  • C9H6Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; Compound 12 can be prepared by Add 24.2g of 4-methoxyphthalic acid to the container,240 ml of dichloromethane,Slowly add 17.9ml of thionyl chloride,After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen;Concentrated under reduced pressure to give compound 12.
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; 24.2 g of 4-methoxyphthalic acid and 240 ml of dichloromethane were added to the container, and 17.9 ml of sulfoxide was slowly added dropwise. After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen; and concentrated to give compound 12 under reduced pressure.
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; Compound 12 can be prepared by: Add 24.2g of 4-methoxyphthalic acid and 240ml of dichloromethane to the container.17.9 ml of thionyl chloride was slowly added dropwise. After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen; and concentrated under reduced pressure to obtain compound 12.
  • 68
  • [ 14963-97-4 ]
  • C25H26O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 °C
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 2.2: 0 - 20 °C
  • 69
  • [ 14963-97-4 ]
  • 2-(1H-benzimidazol-2-ylmethyl)-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 70
  • [ 14963-97-4 ]
  • 4-methoxy-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 71
  • [ 14963-97-4 ]
  • 4-methoxy-2-[2-(pyridin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 72
  • [ 14963-97-4 ]
  • 2-[2-(1H-imidazol-4-yl)ethyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 73
  • [ 14963-97-4 ]
  • 2-[2-(1H-benzimidazol-2-yl)ethyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 74
  • [ 14963-97-4 ]
  • 4-methoxy-2-(3-phenylpropyl)-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 75
  • [ 14963-97-4 ]
  • 2-[3-(1H-benzimidazol-2-yl)propyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 76
  • [ 14963-97-4 ]
  • 2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 77
  • [ 14963-97-4 ]
  • 2-[5-(1H-benzimidazol-2-yl)pentyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 78
  • [ 14963-97-4 ]
  • 2-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 79
  • [ 14963-97-4 ]
  • 2-[2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 80
  • [ 14963-97-4 ]
  • 2-[2-(octahydroisoquinolin-2(1H)-yl)ethyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 81
  • [ 14963-97-4 ]
  • 2-[3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 82
  • [ 14963-97-4 ]
  • 2-[3-(3,4-dihydroisoquinolin-2(1H)-yl)propyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 83
  • [ 14963-97-4 ]
  • 2-[3-(octahydroisoquinolin-2(1H)-yl)propyl]-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
  • 84
  • [ 14963-97-4 ]
  • 2-benzyl-4-methoxy-1H-isoindole-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux
  • 85
  • [ 14963-97-4 ]
  • [ 1158949-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux
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