Acetic Anhydride → 4-[(3-Bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrile

HRID 548417Notes

Reaction equation

HRID 548417 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([CH3:22])[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:9]2[C:18]3[C:13](=[C:14]([CH3:22])[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[C:34](=[O:36])[CH3:35])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 101104774-[(3-Bromophenyl)amino]-8-methyl-6-nitro-quinoline-3-carbonitrile

Product 1

HCID 224667474-[(3-Bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 4-[(3-bromophenyl)amino]-8-methyl-6-nitro-quinoline-3-carbonitrile (15.3 g, 40 mmol), 0.37 g (3 mmol) of dimethylaminopyridine, 40 ml of acetic anhydride, and 80 ml of pyridine was refluxed for 3 h and concentrated at 50° C. under vacuum. The residue was stirred with methylene chloride and 0.1 N HCl. After filtration through Celite, the organic layer was washed with water, dried and concentrated. The residue was subjected to chromatography on silica gel with 1% acetic acid in methylene chloride to give 11.2 g of an amber glass, NMR (CDCl3) d 2.29 (N-acetyl group).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated at 50° C. under vacuum
  3. filtrationAfter filtration through Celite
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12437c90127d489bbc0c907c68d71585
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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