Water → [5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetic acid

HRID 883652Notes

Reaction equation

HRID 883652 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH:16]([C:21]#[N:22])[C:17]([O:19]C)=[O:18])[CH2:12][N+:13]([O-:15])=[O:14].[OH-].[K+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH:16]([C:21]#[N:22])[C:17]([OH:19])=[O:18])[CH2:12][N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 24827441methyl [5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetate

Product 1

HCID 24828184[5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl [5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetate, intermediate 27 (5.00 g; 15.45 mmol) in MeOH (150 ml) was added a potassium hydroxide solution in water (9.27 ml; 5.00 M; 46.34 mmol). After stirring for 2.5 l the solvent was evaporated. The residue was taken up with ethyl acetate and the organic phase extracted with 1N HCl, dried (MgSO4) and the solvent removed in vacuo to give the crude [5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetic acid (4.89 g, quant.). This was a mixture of diastereomers, which was sufficiently pure for subsequent reaction (HPLC purity 93%).

Workup

  1. customwas evaporated
  2. extractionthe organic phase extracted with 1N HCl
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aecc1604b8ea465492b380438cf323f5
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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