m-Aminoacetanilide → HCID 69064422, compound

HRID 2111790Notes

Reaction equation

HRID 2111790 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1.CCN(CC)CC>CCO>[C:22]([NH:21][C:17]1[CH:16]=[C:15]([NH:14][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH:20]=[CH:19][CH:18]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7604m-AminoacetanilideHCID 8471TriethylamineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 69064422HCID 69064422, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluoro-3-nitrobenzoic acid (5) (10.2 g, 54.9 mmol), N-(3-aminophenyl)acetamide (9.21 g, 66.6 mmol) and Et3N (1.4 mL, 10.1 mmol) in anhydrous EtOH (160 mL) was heated at reflux under N2 overnight. The reaction mixture was then cooled and filtered, and the orange solid collected by filtration. It was then washed with 2 M HCl(aq), and dried in vacuo to give 4-{[3-(acetylamino)phenyl]amino}-3-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6): δ 2.03 (s, 3H), 7.02 (d, J=7.9 Hz, 1H), 7.13 (d, J=9.0 Hz, 1H), 7.37 (t, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.68 (s, 1H), 7.93 (dd, J=9.0, 1.9 Hz, 1H), 8.62 (s, 1H), 9.76 (s, 1H), 10.08 (s, 1H), 13.02 (br, 1H); MS (ES+): m/z 316 [MH+]

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 overnight
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. filtrationthe orange solid collected by filtration
  6. washIt was then washed with 2 M HCl(aq)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7fb3c2d3fdf4445b9696ebe3c14bca6f
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

Loading…