m-Aminoacetanilide → HCID 69064422, compound

HRID 2111808Notes

Reaction equation

HRID 2111808 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 (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 atmosphere. After 16 h, the reaction mixture was cooled and the resultant precipitate filtered. The orange solid was washed with 2 M aq HCl and dried to yield 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 (brs, 1H). MS (ES+): m/z 316 [MH+].

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 atmosphere
  3. temperaturethe reaction mixture was cooled
  4. filtrationthe resultant precipitate filtered
  5. washThe orange solid was washed with 2 M aq HCl
  6. customdried

Sources & evidence

ORD record
ord-d927ef901a0f4039a6234c48c2586008
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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