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Chemical Structure| 61-70-1
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Product Details of [ 61-70-1 ]

CAS No. :61-70-1 MDL No. :MFCD00030253
Formula : C9H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :RSQUAQMIGSMNNE-UHFFFAOYSA-N
M.W : 147.17 Pubchem ID :6096
Synonyms :

Calculated chemistry of [ 61-70-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.64
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.59 mg/ml ; 0.0176 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 16.0 mg/ml ; 0.109 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.425 mg/ml ; 0.00289 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 61-70-1 ]

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 [ 61-70-1 ]

* 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 [ 61-70-1 ]
  • Downstream synthetic route of [ 61-70-1 ]

[ 61-70-1 ] Synthesis Path-Upstream   1~67

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Reference: [1] Chemical Communications, 2018, vol. 54, # 59, p. 8265 - 8268
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  • [ 97207-47-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 1,23
  • 3
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YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide In water at 40 - 100℃; for 0.5 h; Heating / reflux To 5 L 4-neck flask (equipped with a mechanical stirrer, condenser and N2 inlet) was charged with 2 L water and 50percent sodium hydroxide (NAOH) (2.52 mol, 201.6 g, 2.25 equiv) followed by oxindol (1.12 mol, 150 g, 1 equiv) and the reaction mixture was heated TO-40° C. Dimethylsulfate (1.68 mol, 211.7 g (159 mL), 1.5 equiv) was added slowly via syringe. The addition was slightly exothermic with temperature rising to 53° C. When addition was complete, the reaction mixture was heated to- 100° C and held for 15 minutes (min). The reaction mixture was cooled TO-600 C, and a second portion of dimethylsulfate (0.476 mol, 60 g (45 mL), 0.425 equiv) was added. The reaction mixture was heated TO ~ 100° C and held 15 min. TLC (heptane/ethyl acetate (EtOAc), 1: 1) show methylation was essentially complete. The reaction mixture was cooled TO-50° C and the pH adjusted to-7 with concentrated HCI. The reaction mixture was seeded, cooled to room temperature and allowed to stand overnight. The solids were collected, wash with water (4X) and dried overnight in a vacuum over AT-40° C to give 110.7 g (67percent) of 1-methyl-1, 3-dihydroindol-2-one as a pink solid, mp 84-86° C.
67.3%
Stage #1: With sodium hydride In xylene for 1.5 h; Heating / reflux
Stage #2: for 2 h; Heating / reflux
A stirred mixture of sodium hydride (60percent, 31g, 0.79 mol) in dry xylene (500 mL), under a nitrogen atmosphere, was heated to reflux for 30 min. l,3-Dihydro-indol-2-one 16a (100 g, 0.75 mol) was then slowly added via an addition funnel and stirred at reflux for 1.5 hrs. Dimethyl sulfate (104 g, 0.83 mol) was added drop-wise, whereupon the resulting homogeneous solution was refluxed for an additional 2 hrs. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SC>4, and concentrated under reduced pressure to afford l-methyl-l,3-dihydro-indol-2-one 16b (74 g, 67.3percent). .HNMR (300 MHz, CDC13) 5 7.23-7.31 (m, 2 H), 7.04 (t, J= 7.5 Hz, 1 H), 6.82 (d, J= 7.8 Hz, 1 H), 3.52 (s, 2 H), 3.21 (s, 3 H).[0270] A suspension of NaH (60percent, 70 g, 0.48 mol) in THF (300 mL) was stirred for 10 min at 0 °C. Then a solution of l-methyl-l,3-dihydro-indol-2-one 16b (70 g, 2.88 mol) in THF (200 mL) was added at 0 °C, and the mixture was stirred for 1 h at room temperature. Benzyl-bis-(2-chloro-ethyl)-amine (129 g, 0.48 mol) was added in portions at 0 °C. The mixture was stirred overnight at room temperature, and then was poured into ice-water, extracted with EtOAc. The combined organic layers were dried over IS^SO^ and concentrated under reduced pressure. The residue was purified by column on silica gel (P.E./E.A. 2:1) to give compound 16c (24 g, 16.3percent). lH NMR (300 MHz, CDCI3) 5 7.25-7.42 (m, 7 H), 7.02-7.07 (m, 1 H), 6.83 (d, J= 7.5, 1 H), 3.68 (s, 2 H), 3.19 (s, 3 H), 2.74-2.99 (m, 2 H), 2.66-2.72 (m, 2 H), 1.93-2.01 (m, 2 H), 1.79-1.85 (m, 2 H).[0271] To a solution of compound 16c (12 g, 39.2 mmol) in MeOH (100 mL) was added Pd(OH)2/C (1.5 g, 20percent>) under N2. The suspension was hydrogenated under H2 (50 psi) at room temperature for 4.5 hrs. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the deprotected spiroindolone product 16d (8 g, 94.5percent). ]H NMR (400 MHz, DMSO-rf6) 5 7.46 (d, J= 7.2,1 H), 7.23-7.27 (m, 1 H), 6.96-7.03 (m, 2 H), 3.04-3.14 (m, 5 H), 2.83-2.89 (m, 2 H), 1.61-1.67 (m, 2 H), 1.45-1.51 (m, 2 H). MS (ESI) m/z 217.1 [M+H]+ [0272] 1.0 eq of deprotected spiroindolone 16d (22 mg, 0.10 mmol) was dissolved in anhydrous l,2-dichloroethane:l,2-dimethoxyethane (1.0 mL, 1:1 v/v) and treated with 1.5 N-Carbethoxy-4-tropinone (30 mg, 0.15 mmol), followed by titanium tetraisopropoxide (88 /xL, 85 mg, 0.30mmol). The vial was flushed with nitrogen and stirred at room temperature ~70 h. The reactionwas then diluted with methanol (1.0 mL), cooled in an ice-BbO bath and treated with sodiumborohydride (8 mg, 0.20 mmol). After warming to room temperature and stirring for 90 min, thereaction was further diluted with methanol (2.0 mL), quenched with 1.0 N NaOH (500 juL) andstirred vigorously at room temperature for 10 min. The suspension obtained was centrifuged(3K rpm, 10 min) and the supernatant concentrated under reduced pressure. The residueobtained was dissolved in MeOH:acetonitrile (1250 fiL, 1:1 v/v), filtered, and purified byreverse-phase HPLC (2-40percent CH3CN/0.1percent TFA gradient over 10 min) to yield productcompound no. 149. LC/MS (10-99percent) m/z [M+H]+398.2, retention time 1.93 min.
Reference: [1] Organic Letters, 2012, vol. 14, # 10, p. 2544 - 2547
[2] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3992 - 3995
[3] Chemistry - An Asian Journal, 2017, vol. 12, # 7, p. 734 - 743
[4] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
[5] Tetrahedron Letters, 2001, vol. 42, # 41, p. 7315 - 7317
[6] Patent: WO2004/37820, 2004, A1, . Location in patent: Page 25; 36-37
[7] Patent: WO2006/23852, 2006, A2, . Location in patent: Page/Page column 107; 108
[8] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7568 - 7573
[9] Itsuu Kenkyusho Nempo, 1956, # 7, p. 7,10; engl. Ref. S. 44, 48[10] Chem.Abstr., 1957, p. 2823
[11] Journal of Organic Chemistry, 1991, vol. 56, # 13, p. 4218 - 4223
[12] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2595 - 2598
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Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12084 - 12085
[2] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[3] Journal of Chemical Research, Miniprint, 1988, # 9, p. 2017 - 2063
[4] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 1, p. 128 - 136
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 446
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 174 - 179
[7] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 911 - 915
  • 5
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YieldReaction ConditionsOperation in experiment
47% for 3 h; Reflux General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60–70°C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95percent) togive N-alkylated isatins as red crystalls in 37–92percent yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2–4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4·H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47–96percent yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60percent dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of –15 °C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3'-indolin]-2'-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3'-indolin]-2'-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7–11).
Reference: [1] Synthetic Communications, 1994, vol. 24, # 20, p. 2835 - 2841
[2] Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1828 - 1834
[3] Tetrahedron Letters, 2018, vol. 59, # 37, p. 3409 - 3412
[4] Heterocycles, 1996, vol. 43, # 1, p. 7 - 10
[5] Patent: US2006/30609, 2006, A1, . Location in patent: Page/Page column 9
[6] Patent: US2006/229348, 2006, A1, . Location in patent: Page/Page column 9
[7] Tetrahedron, 2011, vol. 67, # 5, p. 982 - 989
[8] J.Shinshu Univ., 1951, vol. 1, p. 1,4
[9] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[10] Organic Letters, 2016, vol. 18, # 20, p. 5232 - 5235
[11] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1071 - 1082
[12] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
[13] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
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YieldReaction ConditionsOperation in experiment
98% With hydrazine hydrate In ethanol; water at 45℃; for 0.166667 h; General procedure: A mixture of substitutedisoindigo (0.2 mmol) and hydrazine hydrate (3 ml) in freshly distilled EtOH(3 ml) was heated at 45 C for 10 min. The solvent and volatiles wereevaporated to afford pure products as white solids which did not need to bespecially purified.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6615 - 6618
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YieldReaction ConditionsOperation in experiment
66.6%
Stage #1: for 2 h; Reflux
Stage #2: at 70 - 210℃; for 1.66667 h;
N-methylaniline (20 mL, 186 mmol) was dissolved in toluene (250 mL), and chloroacetyl chloride (15.8 mL, 198 mmol) was added slowly. Then the mixture was refluxed for 2h. Water (50 mL) was added after the mixture was cooledto room temperature and the mixture was stirred for 3h to decompose the chloroacetylchloride. Toluene layer was washed first with 10percent K2CO3 in water solution. And it wascontinuously added with HCl (2M) before drying overnight with sodium sulfate. Aftertoluene was evaporated, AlCl3 (82 g) was added, and the mixture was stirred for 10 minat 70. Then the above mixture was stirred at 210 for 90 min. The reaction mixture wasslowly poured into ice water, and then concentrated HCl (50 mL) was added. The mixturewas extracted with chloroform and chloroform layer was dried over sodium sulfate. Afterevaporating chloroform, the solid was recrystallized with hexane. N-methyloxindole (16 g)was prepared in total yield 66.6percent of the two step. 1H-NMR (300MHz, CDCl3) δ(ppm) : 7.29–7.20 (m, 2H), 7.05–7.00 (t, 1H), 6.81–6.78(d, 1H), 3.47 (s, 2H), 3.18 (s, 3H).
Reference: [1] Ultrasonics Sonochemistry, 2011, vol. 18, # 5, p. 1143 - 1147
[2] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
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YieldReaction ConditionsOperation in experiment
90% With 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one In 1,4-dioxane; water at 140℃; for 5 h; 0.4 mL of 1,4-dioxane was added to a 50 mL reaction tube at room temperature.Add 2mL of water,Stir and mix,Weighing 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one (175 mg, 0.66 mmol) was added to the reaction tube and stirred for 1 min.After the reaction tube was placed in a 140 ° C oil bath,Was added N- methylindole (78mg, 0.6mmol),And with a built-in condenser, react in a 140 ° C oil bath for 5 hours.The TLC dot plate showed complete reaction of the starting material.Take the reaction tube out of the oil bath and cool to room temperature.The reaction was quenched by the addition of 10 mL of saturated sodium bicarbonate.Extracted with 20 mL of ethyl acetate.The organic layer was combined, dried over anhydrous sodium sulfate and evaporated.The yellow solid N-methyl-2-indanone 79 mg was obtained by column chromatography to give a yield of 90percent.
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1437 - 1442
[2] Patent: CN108129377, 2018, A, . Location in patent: Paragraph 0016-0017; 0019; 0021; 0023; 0025; 0027; 0029
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1990, # 4, p. 597 - 603
[4] Journal of the American Chemical Society, 2017, vol. 139, # 34, p. 11887 - 11894
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YieldReaction ConditionsOperation in experiment
59.1% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; Add diethyl azodicarboxylate (DEAD, 8.0 g, 44.9 mmol) dropwise to a solution of indolin-2-one (4.0 g, 30.0 mmol), methanol (1.4 g, 44.9 mmol) and triphenylphosphine (12.0 g, 44.9 mmol) in THF (40 mL) at 0° C., stir the reaction at room temperature overnight.
Concentrate under reduced pressure, purify the resulting residue with flash chromatography (silica gel, EtOAc:PE=1:3) to afford the title compound (2.6 g, 59.1percent). MS: (M+1): 148.2.
Reference: [1] Patent: US2015/197511, 2015, A1, . Location in patent: Paragraph 0298; 0299
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Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
[2] Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3402 - 3415
[3] Journal of the American Chemical Society, 1980, vol. 102, # 10, p. 3646 - 3647
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Reference: [1] Helvetica Chimica Acta, 1993, vol. 76, # 8, p. 2803 - 2813
[2] Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 1017 - 1022
[3] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6887 - 6892
[4] Synthesis, 2011, # 5, p. 723 - 730
[5] Tetrahedron Letters, 2017, vol. 58, # 34, p. 3390 - 3393
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Reference: [1] Organic Letters, 2004, vol. 6, # 16, p. 2785 - 2788
  • 13
  • [ 59-48-3 ]
  • [ 74-88-4 ]
  • [ 61-70-1 ]
Reference: [1] Patent: US2008/15179, 2008, A1, . Location in patent: Page/Page column 136-137
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Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 1, p. 165 - 178
[2] Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3402 - 3415
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Reference: [1] Organic Letters, 2012, vol. 14, # 23, p. 5832 - 5835
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  • [ 579-10-2 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 19, p. 6546 - 6553
[2] Journal of the Chemical Society, Chemical Communications, 1995, # 9, p. 977 - 978
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 33, p. 7244 - 7248
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  • [ 38118-70-6 ]
  • [ 61-70-1 ]
YieldReaction ConditionsOperation in experiment
20% at 70℃; for 12 h; To a 10-mL oven-dried vial containing a magnetic stirring bar, isatin 2a (35.6 mg,0.15 mmol), and PhCF3 (1.0 mL), was added a solution of diazo compound 1a (52.6mg, 0.3 mmol) in PhCF3 (1.0 mL) via a syringe pump in 50 min at 90 oC. After the addition, the reaction mixture was monitored by proton NMR after the solvent was evaporated in vacuo at different reaction times (the time including the 50 min for the addition of 1a)
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 34, p. 3390 - 3393
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Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
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YieldReaction ConditionsOperation in experiment
8 mg With oxone In water; acetone for 2 h; General procedure: An oven-dried 10 mL microwave vial was charged with R-BMIDA (0.1 mmol, 1 equiv) before the addition MeOH (4 mL). The vial was capped before the addition of KHF2 (100 μL, 4.5 M aq. solution, 0.5 mmol, 5 equiv). The solution was then heated to 70 °C for 4 h, then cooled, vented, decapped, and the MeOH solution was transferred to a clean flask and concentrated under reduced pressure to provide a white solid. The residue was diluted with hot acetone and the BF3K solution was transferred to a 5 mL flask (2 × 2 mL acetone) and concentrated under reduced pressure. The resulting residue was diluted with acetone (0.5 mL) before the addition of Oxone (35 mg, 0.11 mmol, 1.1equiv) in H2O (0.5 mL). The reaction was stirred for 2 h before the addition of 1 M HCl (2 mL). The reaction mixture was then diluted with H2O (2 mL) and extracted with CH2Cl2 (2 × 5 mL). The organic layers were filtered through 2 cm of silica gel and washed with CH2Cl2 (20 mL). The resulting solution was concentrated under vacuum to afford the desired product.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 4, p. 891 - 898
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Reference: [1] RSC Advances, 2017, vol. 7, # 71, p. 45227 - 45231
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Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6497 - 6507
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 174 - 179
[3] Helvetica Chimica Acta, 1993, vol. 76, # 8, p. 2803 - 2813
[4] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1163 - 1166
[5] Synthesis, 2011, # 5, p. 723 - 730
[6] Chemical Communications, 2011, vol. 47, # 40, p. 11336 - 11338
[7] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6887 - 6892
[8] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
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Reference: [1] Organic Letters, 2008, vol. 10, # 6, p. 1163 - 1166
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Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[2] Organic Letters, 2016, vol. 18, # 20, p. 5232 - 5235
[3] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
[4] Tetrahedron Letters, 2018, vol. 59, # 37, p. 3409 - 3412
[5] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
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YieldReaction ConditionsOperation in experiment
53% for 1 h; Reflux 1,3-Dimethyl-5-propylaminomethylenepyrimidine-2,4,6-trione (6a) (Method B) The mixture of 1-propylamine (0.17 mL, 2 mmol), 1,3-dimethylbarbituric acid 2a 0.312 g, 2 mmol) and triethyl orthoformate (0.4 mL, 2.5 mmol) was refluxed for 15 min in EtOH (2.5 mL). Filtered residue of 6a was recrystallized from EtOH, to give 6a
Reference: [1] Heterocycles, 2015, vol. 91, # 1, p. 64 - 75
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Reference: [1] Patent: US5478842, 1995, A,
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2763 - 2766
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  • [ 3265-27-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 74, p. 70221 - 70225
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Reference: [1] Organic Letters, 2004, vol. 6, # 16, p. 2785 - 2788
  • 30
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Reference: [1] Organic Letters, 2004, vol. 6, # 16, p. 2785 - 2788
  • 31
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Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
[2] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
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Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
[2] Journal of the American Chemical Society, 1985, vol. 107, # 2, p. 435 - 443
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YieldReaction ConditionsOperation in experiment
58% With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 3 h; N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58percent yield.1H-NMR (300MHz, CDCl3) δ(ppm) : 7.42–7.39 (d, 1H), 7.26 (s, 1H), 6.71–6.68 (d,1H), 3.52–3.20 (s, 2H), 3.19 (s, 3H).
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