3-Aminobenzonitrile → HCID 178509847, compound

HRID 24804

Reaction equation

HRID 24804 reaction equation
C([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[C:11](=[C:21](O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]1=[O:29])(=O)C1C=CC=CC=1.[NH2:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[C:34]#[N:35]>CN(C=O)C>[C:34]([C:33]1[CH:32]=[C:31]([NH:30]/[C:21](=[C:11]2\[C:10](=[O:29])[NH:9][C:17]3[C:12]\2=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)/[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:38]=[CH:37][CH:36]=1)#[N:35]

Participants

4

Reactant 2

HCID 167023-AminobenzonitrileHCID 178516550HCID 178516550, compound

Product 1

HCID 178509847HCID 178509847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (5.2 mmol) of 1-benzoyl-3-(1-hydroxy-1-phenyl-methylidene)-5-nitro-2-indolinone and 1.8 g (16 mmol) of 3-aminobenzonitrile are stirred in DMF for 70 hours at ambient temperature. Then the reaction solution is extracted with ether, the organic phase is washed with water and dried over sodium sulphate. After removal of the solvent in vacuo the residue is chromatographed on silica gel (dichloromethane/methanol=50:1).

Workup

  1. extractionThen the reaction solution is extracted with ether
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. customAfter removal of the solvent in vacuo the residue
  5. customis chromatographed on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-bdb4ef81648c47fd8675561909d34a08
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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