Acetic Anhydride → N-[3-(4-Cyano-phenyl)-6-nitro-indol-1-yl]-acetamide

HRID 2079905Notes

Reaction equation

HRID 2079905 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[C:11]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:10]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[C:25]([C:24]1[CH:23]=[CH:22][C:21]([C:11]2[C:12]3[C:17](=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)[N:9]([NH:8][C:5](=[O:7])[CH3:6])[CH:10]=2)=[CH:28][CH:27]=1)#[N:26]

Participants

6

Reactant 3

HCID 7918Acetic Anhydride2×HCID 81531Diisopropylethylamine2×HCID 574422614-(1-amino-6-nitro-1H-indol-3-yl)-benzonitrile

Product 1

HCID 57442262N-[3-(4-Cyano-phenyl)-6-nitro-indol-1-yl]-acetamideYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add acetic anhydride (214 mg, 2.1 mmol) to a mixture of 4-(1-Amino-6-nitro-1H-indol-3-yl)-benzonitrile (400 mg, 1.4 mmol) and di-isopropylethylamine (194 mg, 2.1 mmol) and N,N-dimethylaminopyridine (2 mg) in DMF (20 mL) and stir for 3 h. Add additional acetic anhydride (214 mg, 2.1 mmol) and di-isopropylethylamine (194 mg, 2.1 mmol) and stir overnight. Dilute the mixture with water and extract with EtOAc. Wash the combined extracts with water and brine, and dry over MgSO4. Purify the crude residue using silica gel chromatography to give 170 mg (38% yield) of N-[3-(4-Cyano-phenyl)-6-nitro-indol-1-yl]-acetamide.

Workup

  1. stirringstir overnight
  2. extractionextract with EtOAc
  3. washWash the combined extracts with water and brine
  4. dry with materialdry over MgSO4
  5. customPurify the crude residue

Sources & evidence

ORD record
ord-6864b6321a7745a8b091e9ba25173e48
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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