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

HRID 883653Notes

Reaction equation

HRID 883653 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:20]#[N:21])C(O)=O)[CH2:12][N+:13]([O-:15])=[O:14]>CN(C=O)C>[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([CH2:16][C:20]#[N:21])[CH2:12][N+:13]([O-:15])=[O:14]

Participants

3

Reactant 1

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

Product 1

HCID 24828728[5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [5-chloro-3-(nitromethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetic acid, intermediate 28 (2.00 g; 6.46 mmol) in anhydrous DMF (15 ml) was heated at 160° C. for 1 hour. After evaporation of the solvent, the residue was taken up in ethyl acetate, extracted with brine, 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]acetonitrile (1.74 g, quant, HPLC purity 93%). MS (ESI−): 264.1

Workup

  1. customAfter evaporation of the solvent
  2. extractionextracted with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-040ab8747f4c4ee79d301d7dbdf55e19
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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