Sodium Hydroxide → HCID 797803, compound

HRID 599503Notes

Reaction equation

HRID 599503 reaction equation
[C:1]([C:3]([C:20](=[O:28])[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]([O:17]CC)=[O:16])[CH:6]=1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1](/[C:3](/[C:20](=[O:28])[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:4]\[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]([OH:17])=[O:16])[CH:6]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 3136896HCID 3136896, compound

Product 1

HCID 797803HCID 797803, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of crude ethyl [3-(2-cyano-2-phenylcarbamoyl-vinyl)-indol-1-yl]-acetate (0.079 mmol) in THF (0.8 ml) is treated with 0.2N aqueous NaOH (0.4 ml, 0.08 mmol) at rt for 10 min. The yellow reaction mixture is diluted with water (2 ml) and washed twice with diethyl ether (2 ml). The aqueous phase is acidified to pH 1 by adding conc. HCl and extracted with dichloromethane. The solvent is evaporated and the residue is recrystallized from acetonitrile yielding pure title compound.

Workup

  1. washwashed twice with diethyl ether (2 ml)
  2. additionby adding conc. HCl
  3. extractionextracted with dichloromethane
  4. customThe solvent is evaporated
  5. customthe residue is recrystallized from acetonitrile yielding pure title compound

Sources & evidence

ORD record
ord-9c7d7d82caad447589acc40fd77e538c
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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