Ethanol → HCID 66604433, compound

HRID 2410664Notes

Reaction equation

HRID 2410664 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17]([O:19]CC)=[O:18])=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[OH-].[Na+].CCO>C1COCC1>[C:1]([C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17]([OH:19])=[O:18])=[CH:10][C:9]2=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66604388HCID 66604388, compound

Product 1

HCID 66604433HCID 66604433, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazole-3-carboxylate (980 mg, 2.294 mmol), 1 M aqueous sodium hydroxide (5.73 mL, 5.73 mmol) in THF (13 mL)/EtOH (13 mL) was heated in an oil bath at 85° C. for 24 h. The solvent was removed under reduced pressure. The solid was suspended in water (200 mL). To this suspension was added aqueous 1N HCl solution until pH ˜2-3. The solid was collected by filtration and dried. The crude was purified using silica gel column chromatography (CH2Cl2-MeOH-3 to 50%) to afford 820 mg of 8-carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazole-3-carboxylic acid which was used as such in the next reaction. MS (ESI) m/z 397.2 (M−H). 1H NMR (DMSO-d6) δ ppm 12.64 (1H, br. s.), 11.80 (1H, s), 8.83-9.08 (2H, m), 8.42 (1H, br. s.), 8.39 (1H, s), 8.29 (1H, d, J=2.14 Hz), 8.03-8.07 (1H, m), 8.00 (1H, dd, J=8.55, 2.14 Hz), 7.74-7.81 (2H, m), 7.63 (1H, br. s.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionTo this suspension was added aqueous 1N HCl solution until pH ˜2-3
  3. filtrationThe solid was collected by filtration
  4. customdried
  5. customThe crude was purified

Sources & evidence

ORD record
ord-bb52e648ae33405b89f5c44f9059ee64
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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