O-Toluidine → N-acetyl-o-toluidine

HRID 572128Notes

Reaction equation

HRID 572128 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[C:10]([CH3:15])=[CH:11][CH:12]=[CH:13][CH:14]=1>ClCCl>[C:10]1([CH3:15])[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:5](=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 7918Acetic Anhydride

Product 1

HCID 8443N-acetyl-o-toluidineYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (33.0 mL, 350 mmol) was added to a stirred solution of o-toluidine (30.0 g, 280 mmol) in dichloromethane (500 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 20 h. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine, then dried (MgSO4) and evaporated in vacuo. The residue was stirred in isohexane at 0° C. for 2 h, then filtered. The precipitate was washed with isohexane and dried under vacuum. The title compound (39.87 g, 95%) was obtained as a pale pink solid. δH (CDCl3) 7.80-7.78 (m, 1H), 7.26-7.20 (m, 2H), 7.13-7.08 (m, 1H), 6.92 (br s, 1H), 2.29 (s, 3H), 2.23 (s, 3H). LCMS (ES+) 150 (M+H)+, RT 0.85 minutes.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. stirringThe residue was stirred in isohexane at 0° C. for 2 h
  6. filtrationfiltered
  7. washThe precipitate was washed with isohexane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-43e33d2d18e34937aed4d07318fdf924
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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