Sodium Hydroxide → 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylic acid

HRID 2410672Notes

Reaction equation

HRID 2410672 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([O:19]CC)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66605544ethyl 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylate

Product 1

HCID 666057668-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylate (2.1 g, 5.41 mmol) in a mixture of THF (40 mL) and MeOH (14 mL) was added a solution of aq. 1 M sodium hydroxide (13.52 mL, 13.52 mmol). The mixture was stirred at room temperature for 2 days. Removal of solvents left a solid which was suspended in water (150 mL), This was acidified with 1N HCl to pH 2-3 and the solid was collected by filtration, washed with H2O(3×20 mL), and dried under vacuum to afford 1.78 gm of the desired product (83% yield). MS (ESI) m/z 361.1 (M+H). 1H NMR (DMSO-d6) δ ppm 12.79 (1H, br. s.), 11.70 (1H, s), 8.76 (1H, s), 8.38-8.47 (2H, m), 8.35 (2H, dd, J=4.58, 3.36 Hz), 7.82 (1H, d, J=7.93 Hz), 7.59 (1H, br. s.), 7.40-7.52 (3H, m), 6.96 (1H, dd, J=7.93, 2.14 Hz), 3.89 (3H, s).

Workup

  1. customRemoval of solvents
  2. waitleft a solid which
  3. filtrationthe solid was collected by filtration
  4. washwashed with H2O(3×20 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c65c4fdf79a54b568a3d1aef0b481ffc
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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