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Product Details of [ 89-40-7 ]

CAS No. :89-40-7 MDL No. :MFCD00005884
Formula : C8H4N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ANYWGXDASKQYAD-UHFFFAOYSA-N
M.W : 192.13 Pubchem ID :6969
Synonyms :

Calculated chemistry of [ 89-40-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.64
TPSA : 91.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.52
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 0.1
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : -0.66
Consensus Log Po/w : 0.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.9
Solubility : 2.42 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (Ali) : -2.5
Solubility : 0.608 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.32 mg/ml ; 0.00689 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 89-40-7 ]

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

Application In Synthesis of [ 89-40-7 ]

* 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.

  • Upstream synthesis route of [ 89-40-7 ]
  • Downstream synthetic route of [ 89-40-7 ]

[ 89-40-7 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 89-40-7 ]
  • [ 64169-34-2 ]
Reference: [1] Patent: US2011/77394, 2011, A1,
[2] Patent: CN108383833, 2018, A,
  • 2
  • [ 89-40-7 ]
  • [ 65399-05-5 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 26, p. 7485 - 7496
[2] Patent: WO2006/103550, 2006, A1, . Location in patent: Page/Page column 8-9
[3] Patent: US2011/77394, 2011, A1,
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 53 - 56
[5] Patent: CN108383833, 2018, A,
  • 3
  • [ 89-40-7 ]
  • [ 3676-85-5 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In DMF (N,N-dimethyl-formamide) at 20 - 50℃; 4-Nitrophthalimide (LOOGR) was taken into a hydrogenation vessel and dissolved using 600ML OF DIMETHYLFORMAMIDE. Raney nickel catalyst (20gr, wet) was added to the solution and hydrogenated initially at 20-30°C under 20-40psi pressure. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50°C. After the hydrogenation is over the reaction mixture was filtered while hot and the catalyst removed by filtration. Dimethylformamide was removed from the filtrate under reduced pressure at 60-80°C. Water (500ML) was added to the residue and the mixture stirred for 20-30MIN. The product was isolated by filtration and dried at 60-70°C to get a yellow crystalline solid of 4-aminophthalimide (82gr, 97percent). Melting point: 293-5°C.
97% With hydrogen In ethyl acetate The synthesis of bromoacetal 6 from phthalimide (7) is shown in FIG. 11. Based on reactions described in the literature, these transformations were carried out on large scale, and some steps were improved. Nitration of 200 g of phthalimide (7) gives 146 g of 5-nitrophthalimide (8). Reduction of 8 by catalytic hydrogenation, according to the literature procedure, is a bottleneck in the synthesis because of the large volume of solvent needed. With a 2 L Parr hydrogenator pressure vessel, 30 g of 8 is converted to 25 g of amine 9. The next step is also a reduction; aminophthalide 10 is obtained quantitatively from 9 by copper-catalyzed reaction with zinc in aqueous base. Steps b and c could be combined by treating 8 with zinc dust and copper(II) sulfate in 2 M aq. sodium hydroxide. This variation, which is not shown in FIG. 11, removes the bottleneck, potentially allowing 100 g of 10 to be prepared in one step from 146 g of 9. The reaction conditions for the steps shown in FIG. 11 are as follows: a) HNO3, H2SO4, 0° C., 56percent ; b) 5percent Pd/C, H2, EtOAc, 97percent ; c) Zn, CuSO4, 6 M NaOH, 5° C. then heated at 70-80° C. 16 h, 100percent ; d) NaNO2, 4 M HBr, followed by CuBr at 0° C.; e) DIBAL, toluene, -42° C.; f) BF3 OEt2, MeOH, RT.
95% With hydrogen In DMF (N,N-dimethyl-formamide) at 20 - 50℃; 4-Nitrophthalimide (LOOGR) was taken into a hydrogenation kettle and dissolved using 700ML of dimethylformamide. 5percent PALLADIUM/CARBON (LOGR, 50percent wet) was added to the solution and hydrogenated initially at 20-30°C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50°C. After the hydrogenation was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Dimethylformamide was removed from the filtrate under reduced pressure at 60-80°C. Water (500ML) was added to the residue and the mixture stirred for 30MIN. The product was isolated by filtration and dried at 60-70°C to get 80gr (95percent) of yellow crystalline solid of 4- aminophthalimide. Melting point: 294-5°C.
94% With hydrogenchloride; tin(ll) chloride In water at 0 - 55℃; for 3 h; Stannous chloride (0.364 mol) was dissolved in 82.0 ml of concentrated hydrochloric acid at 0 °C and the intermediate compound 2 (0.104 mol) add slowly, and slowly warm to 55 ° C. after stirring for 3 hours, and cool to 0 ° C, add sodium hydroxide (0.832 mol) control solution temperature does not exceed 12 ° C, precipitation of yellow solid, filter, filter cake washed with warm water 3 times, dry, intermediate compound 3, yellow solid, yield 94 percent
92.5% With hydrogen In methanol; DMF (N,N-dimethyl-formamide) at 25 - 50℃; 4-Nitrophthalimide (LOOGR) was taken into a beaker and dissolved using 300ML of dimethylformamide and 400ML of methanol. The solution was transferred into a 1L hydrogenation kettle and 20gr of wet Raney nickel catalyst was charged into the kettle. Hydrogenation was carried out initially at 20-40psi and 25-30°C until the exothermic nature was over. Hydrogenation was further continued at 40-60psi pressure and 40-50°C. After checking the completion of reaction by TLC, catalyst was removed by filtration and the solvents distilled off from the reaction mixture at 50-60°C. The residue thus obtained was suspended in water (500ML) and filtered off to get a bright yellow crystalline compound of 4-aminophthalimide (78gr, 92.5percent). Melting point: 294-5°C.
92% With hydrogenchloride; tin(II) chloride dihdyrate In water at 40℃; for 1 h; Add 112.8 g of stannous chloride dihydrate and 70 mL of concentrated hydrochloric acid to a 500 mL three-necked flask, and stir until completely dissolved.19.2 g of 4-nitrophthalimide was added, and the reaction was stopped after reacting at 40 ° C for 1 h.The reaction solution was suction filtered to obtain a filter residue, and the filter residue was washed twice with 50 mL of concentrated hydrochloric acid and then dried.After washing twice with 50 mL of ethyl acetate, a second suction filtration was performed.The filter residue obtained by the second suction filtration was dried to obtain 14.9 g of 4-aminophthalimide yellow powder, and the yield was 92percent.
89.03% With iron; ammonium chloride In ethanol; water at 65℃; for 4 h; In a 250 ml two-necked flask, 40 ml of absolute ethanol and 10 ml of distilled water, 14.56 g (0.26 mol) of iron powder and 1.643 g (0.031 mol) of ammonium chloride were added.10g (0.052mol) of 4-nitrophthalimide was added under stirring without nitrogen protection; the temperature was set at 65 ° C, and the reaction was about 4 h.TCL shows that the disappearance of the starting point of the reaction is completed; the pH of the solution is adjusted to 9-10 by sodium carbonate, the filter cake is filtered and dried, and extracted with 100 ml of absolute ethanol (85 ° C) for 3 times.Ethanol distilled under reduced pressure to give a yellow solid 7.5g, yield 89.03percent.
89% With hydrogenchloride; tin(ll) chloride In water at 50℃; for 2 h; 5: A mixture of 4-nitro-phthalimide 4 (8.02 g, 0.042 mol) and hydrochloric acid (26 percent, 290 mL) was heated at 50 °C for 2 h. Then the resulted yellow solution was cooled to room temperature. The precipitate was collected by filtration and recrystallized from ethanol dried in vacuum affording a light yellow solid 5 (7.44 g, 89percent yield). 1H NMR (DMSO-d6): δ (ppm) 10.77 (s, 1H, CONHCO), 7.45 (d, J1 = 8.0, 1H, Ar-H), 6.92 (d, J2 = 2.0 Hz, 1H, Ar-H), 6.86 (dd, J1= 8.0, J2 = 2.0 Hz, 1H, Ar-H). 5.06 (s, 2H, NH2). 13CNMR (DMSO-d6): δ (ppm) 169.44, 169.26, 150.64, 135.22, 124.73, 121.51, 120.11, 109.64.
98 %Chromat. With hydrogen In tetrahydrofuran; water at 100℃; for 16 h; Autoclave General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

Reference: [1] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 8
[2] Patent: US2011/77394, 2011, A1, . Location in patent: Page/Page column 15
[3] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 9
[4] ChemCatChem, 2017, vol. 9, # 6, p. 1128 - 1134
[5] Patent: CN104447496, 2017, B, . Location in patent: Paragraph 0067; 0070; 0071
[6] Patent: WO2004/43919, 2004, A1, . Location in patent: Page 8
[7] Patent: CN107778211, 2018, A, . Location in patent: Paragraph 0027-0035; 0036; 0037; 0038; 0039-0056
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 53 - 56
[9] Chemical Communications, 2012, vol. 48, # 64, p. 7982 - 7984
[10] Patent: CN108383833, 2018, A, . Location in patent: Paragraph 0011
[11] Chinese Chemical Letters, 2018, p. 331 - 335
[12] Tetrahedron, 1998, vol. 54, # 26, p. 7485 - 7496
[13] Green Chemistry, 2015, vol. 17, # 2, p. 898 - 902
[14] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[15] Macromolecules, 2002, vol. 35, # 12, p. 4636 - 4645
[16] Journal of the Chemical Society, 1931, p. 79,81
[17] Patent: US2009/143372, 2009, A1,
[18] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1261 - 1264
[19] Chinese Journal of Catalysis, 2016, vol. 37, # 1, p. 91 - 97
[20] MedChemComm, 2016, vol. 7, # 2, p. 292 - 296
[21] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65
  • 4
  • [ 89-40-7 ]
  • [ 3676-85-5 ]
Reference: [1] Chemical Communications, 2004, # 20, p. 2338 - 2339
[2] Chemical Communications, 2005, # 14, p. 1901 - 1903
  • 5
  • [ 89-40-7 ]
  • [ 50727-06-5 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 79,81
  • 6
  • [ 89-40-7 ]
  • [ 7147-90-2 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 79,81
[2] Patent: CN104447496, 2017, B,
[3] Chinese Chemical Letters, 2018, p. 331 - 335
  • 7
  • [ 89-40-7 ]
  • [ 2307-00-8 ]
Reference: [1] Chemische Berichte, 1984, vol. 117, # 6, p. 2275 - 2286
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2022 - 2026
  • 8
  • [ 89-40-7 ]
  • [ 3682-14-2 ]
Reference: [1] Patent: CN106810501, 2017, A,
  • 9
  • [ 136918-14-4 ]
  • [ 89-40-7 ]
YieldReaction ConditionsOperation in experiment
94% at 10 - 25℃; for 12 h; Phthalimide (80 g)was added into mixed acid which prepared from fuming nitric acid(65percent,100 g) and concentrated sulfuric acid (98percent, 500 g) at 10° C. Thereaction mixture was then allowed to warm slowly to 25° C. After12 h, the reaction product was precipitated by pouring into ice(1500 g), filtered and washed with water until free from acid, andpurified by crystallisation from ethanol. Yield: 94percent.
83% at 0 - 35℃; for 4.5 h; The mixture of nitric acid (0.27mol) and sulfuric acid (1.62mol) was stirred in an ice bath maintained for 30min to room temperature [1]. The phtalimide (1) was added dropwise to acidic solution and heated at 35°C while stirring until a colorless solution was achieved. After stirring for 4h, the white solid was precipitated from ice water, filtered and washed with water. The resultant Crude was dried under ambient conditions. 83percent yield; 1H NMR (300MHz, DMSO-d6; δ: ppm): 8.02 (d, J=5.7Hz, 1H, H−Ar); 8.35 (s, 1H, H−Ar); 8.55 (d, J=6.9Hz, 1H, H−Ar); 11.75 (s, 1H, N−H). 13C NMR (75MHz, DMSO-d6, δ): 118.17; 124.93; 129.87; 134.43; 137.66; 151.71; 167.61; 167.92.
64% at 0 - 20℃; for 12 h; The phthalimide (0.227 mil) was slowly added to 100 ml of concentrated sulfuric acid at 0 ° C, The control temperature is no more than 12 ° C. After adding the ice bath to 0 ° C, add 40ml of mixed acid (fuming HNO3/concentrated H2SO4 = 1/1) and the mixture was stirred at room temperature for 12 hours. The reaction solution was poured into 3 times the amount of ice water, and the mixture was stirred and the solid was precipitated. The filter cake was washed three times with water and the residue was recrystallized from 95percent ethanol to give intermediate 2 as a white solid in 64percent ,
61% at 15 - 35℃; for 0.75 h; To fuming, 100percent HNO3 (20 mL), conc H2SO4 (80 mL) was slowly added and the mixturecooled in an ice bath. To the obtained mixture phthalimide (15 g, 0.1 mol) was added in portions over a 15-min interval with stirring at a temperature under 15 °C, then the temperature was raised to about 35 °C and held for 45 min. After completion of the reaction the mixture was cooled to 0 °C and slowly added to ice (375g) at such a rate that the temperature remained below 15 °C. The precipitated crude product was collected byvacuum filtration, washed with cold water, dried at rt and purified by recrystallization from anhydrous EtOH.Pale yellow crystals, yield 61percent, 11.70 g, mp 194.5-195 °C (lit.27 m.p. 194.5-195 °C). 1H NMR (600 MHz, DMSO-d6):δH 8.00 (1Harom, d, 2JHH 5.7 Hz), 8.34 (1Harom, s), 8.54 (1Harom, d, 2JHH 6.9 Hz), 11.76 (1H, s, NH).
56% With sulfuric acid; nitric acid In water at 0℃; The synthesis of bromoacetal 6 from phthalimide (7) is shown in FIG. 11. Based on reactions described in the literature, these transformations were carried out on large scale, and some steps were improved. Nitration of 200 g of phthalimide (7) gives 146 g of 5-nitrophthalimide (8). Reduction of 8 by catalytic hydrogenation, according to the literature procedure, is a bottleneck in the synthesis because of the large volume of solvent needed. With a 2 L Parr hydrogenator pressure vessel, 30 g of 8 is converted to 25 g of amine 9. The next step is also a reduction; aminophthalide 10 is obtained quantitatively from 9 by copper-catalyzed reaction with zinc in aqueous base. Steps b and c could be combined by treating 8 with zinc dust and copper(II) sulfate in 2 M aq. sodium hydroxide. This variation, which is not shown in FIG. 11, removes the bottleneck, potentially allowing 100 g of 10 to be prepared in one step from 146 g of 9. The reaction conditions for the steps shown in FIG. 11 are as follows: a) HNO3, H2SO4, 0° C., 56percent ; b) 5percent Pd/C, H2, EtOAc, 97percent ; c) Zn, CuSO4, 6 M NaOH, 5° C. then heated at 70-80° C. 16 h, 100percent ; d) NaNO2, 4 M HBr, followed by CuBr at 0° C.; e) DIBAL, toluene, -42° C.; f) BF3 OEt2, MeOH, RT.
52% at 80℃; for 1 h; 4: Phthalimide 3 (12.66 g, 0.086 mol) was added to a mixture of concentrated sulfuric acid (78 mL) and fuming nitric acid (5 mL). After heating at 80 °C for 1 hour, the dark red reaction mixture was cooled to r.t. then poured into ice. The resulted white precipitate was filtered and washed with water, recrystallized from ethanol and dried in vacuum to give a white fine crystal 4 (8.30 g, 52percent yield). 1H NMR (DMSO-d6): δ (ppm) 11.83 (brs, 1H, CONHCO), 8.61 (dd, J1 = 8.0, J2= 2.0 Hz, 1H, Ar-H), 8.44 (d, J2= 2.0 Hz, 1H, Ar-H), 8.08 (d, J1= 8.0 Hz, 1H, Ar-H). 13CNMR (DMSO-d6): δ (ppm) 167.49, 167.20, 151.30, 137.23, 133.98, 129.39, 124.40, 117.70.
45.5% With sulfuric acid; nitric acid In water at 0 - 20℃; To a stirred, cold (ice-bath) solution of 22 mL of fuming aqueous nitric acid and 50 mL of concentrated aqueous sulfuric acid was added, portionwise, 14.7 g (0.1 mol) of phthalimide.
The mixture was allowed to warm to room temperature.
After about 3 h, complete solution was obtained.
The yellow solution was slowly poured, with stirring, onto 200 g ice.
The crude product which precipitated was collected by filtration and 4-nitrophthalimide was recrystallized from ethanol to afford 8.74 g (45.5percent) as yellow solid. Mp: 198-202 °C.
61.3% With sulfuric acid; nitric acid In CaCl2 Intermediate 20: 5-Bromoisoindoline
In a dried 50 mL two necked round-bottom flask equipped with an addition funnel and CaCl2 drying tube was placed 2.0 g (13.6 mmol) of phthalimide.
The flask was then cooled to 0° C. in a salt and ice bath.
An ice cold mixture of concentrated sulfuric acid and fuming nitric acid (1:1 v/v) 8 mL was gradually added with constant stirring.
The mixture was then stirred for 30 min. at 0° C. and allowed to slowly warm to room temperature with stirring over a period of 1 h.
The reaction mixture was then poured into ice.
The resulting solid product was filtered and dried to give 1.6 g (61.3percent) of 5-nitro-1H-isoindole-1,3(2H)-dione as a yellow colour solid.

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[8] MedChemComm, 2016, vol. 7, # 2, p. 292 - 296
[9] Patent: CN104447496, 2017, B, . Location in patent: Paragraph 0067-0069
[10] Arkivoc, 2016, vol. 2017, # 2, p. 433 - 445
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[15] Patent: US2011/77394, 2011, A1, . Location in patent: Page/Page column 15
[16] Synthetic Communications, 1989, vol. 19, # 18, p. 3231 - 3240
[17] Chinese Chemical Letters, 2018, p. 331 - 335
[18] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5738 - 5746
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[20] Journal of the Chemical Society, 1931, p. 79,81
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YieldReaction ConditionsOperation in experiment
83% With manganese(IV) oxide; ammonium hydroxide; oxygen; chlorobenzene In N,N-dimethyl-formamide at 100℃; for 24 h; Autoclave; Green chemistry General procedure: 0.01g of MnO2 catalyst, 0.5mmol of 1-indanone, 0.2g of ammonia water (25wtpercent) and 2g of chlorobenzene were added to a stainless steel autoclave with a polytetrafluoroethylene inner liner.The temperature was raised to 110 by automatic temperature controller, 0.6MPa oxygen was added and the reaction was continued for 4h. The pressure was kept constant during the reaction.The reaction product was analyzed using GC-MS with a phthalamide yield of 85percent.
Reference: [1] Patent: CN106278990, 2017, A, . Location in patent: Paragraph 0013; 0017; 0018; 0020; 0024; 0028
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YieldReaction ConditionsOperation in experiment
95% With formamide In neat (no solvent) for 0.25 h; Milling; Heating; Green chemistry General procedure: A mixture of anhydride (1 mmol), formamide (1.1 mmol for monoanhydrides and 2.2 mmol for dianhydrides) and 1 g clay was ground together in a mortar using pestle for the time described in Table 1. The reaction mixture was warmed. After completing the reaction (monitored by TLC, after observing no anhydride presence in the reaction mixture), the product was extracted by washing clay with chloroform (2×15 mL), the solvent was removed under vacuum to afford the relevant N-unsubstituted cyclic imide. The solid imide was washed thoroughly with water, dried, and then recrystallized from ethanol. The solid clay portion was washed with methanol and dried at 120 °C under a reduced pressure to be reused in the subsequent reactions which showed the gradual decrease in the activity (Table 1). Isolated products were characterized by melting points, IR, 1H NMR spectrometric data and were compared with the literature or authentic samples.
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[5] Monatshefte fuer Chemie, 1902, vol. 23, p. 418
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[2] Journal of the Chemical Society, 1937, p. 26,31
[3] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1261 - 1264
[4] Patent: CN106810501, 2017, A, . Location in patent: Paragraph 0048
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[2] Patent: CN106083732, 2016, A,
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  • [ 89-40-7 ]
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[2] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
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Reference: [1] Chemische Berichte, 1900, vol. 33, p. 2811
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YieldReaction ConditionsOperation in experiment
90% at 110℃; for 24 h; Compound 1 was stirred in 32percent ammonia solution (70mL) for 24h. The resulting deep yellow product was filtered and washed with cold water until disappearance of excess of ammonia [1]. The title compound was dried at 110°C. 90percent yield.; 1H NMR (300MHz, DMSO-d6; δ: ppm): 7.63 (s, 2H); 7.71 (d, J=8.1, 1H); 8.02 (s, 1H); 8.08 (s, 1H); 8.29 (dd, J J=2.4Hz, J=8.7Hz, 1H); 8.32 (d, J=2.1Hz, 1H). 13C NMR (75MHz, DMSO-d6, δ): 122.34, 124.38; 129.12; 137.19; 142.65; 147.03; 167.67; 168.67.
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[2] Heterocycles, 1984, vol. 22, # 9, p. 2047 - 2052
[3] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
[4] Acta Chemica Scandinavica, 1999, vol. 53, # 9, p. 714 - 720
[5] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2155 - 2159
[6] Synthetic Communications, 1989, vol. 19, # 18, p. 3231 - 3240
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[8] Journal of the Chemical Society, Chemical Communications, 1992, # 12, p. 873 - 875
[9] Spectrochimica Acta - Part A Molecular Spectroscopy, 1998, vol. 54 A, # 1, p. 77 - 83
[10] Mendeleev Communications, 2002, vol. 12, # 3, p. 96 - 97
[11] Patent: US4056560, 1977, A,
[12] Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 4, p. 573 - 581
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Reference: [1] Journal of the American Chemical Society, 1901, vol. 23, p. 751
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Reference: [1] Patent: CN107188875, 2017, A,
[2] Patent: CN107188875, 2017, A,
[3] Patent: CN107188875, 2017, A,
[4] Patent: CN107188875, 2017, A,
[5] Patent: CN107188875, 2017, A,
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