Acetic Anhydride → HCID 54737396, compound

HRID 462074Notes

Reaction equation

HRID 462074 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:12][CH3:13])[C:5](=[CH:9][C:10]=1[CH3:11])[C:6]([OH:8])=O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(O)(=O)C>[OH:8][C:6]1[C:5]2[C:4](=[CH:3][C:2]([CH3:1])=[C:10]([CH3:11])[CH:9]=2)[N:12]([CH3:13])[C:14](=[O:16])[CH:15]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 213903694,5-Dimethyl-2-(methylamino)benzoic acid

Product 1

HCID 54737396HCID 54737396, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4,5-dimethyl-N-methyl anthranilic acid (30.0g.; 0.168 mole; m.p. 190° - 191° C) in glacial acetic acid (75 ml.) was added acetic anhydride (75 ml.) and the mixture was refluxed for 4 hrs. After cooling the dark solution was poured onto crushed ice, made alkaline (pH 9), and filtered. On bringing the filtrate to pH5 with concentrated hydrochloric acid the title product separated as a white solid, m.p. (EtOH) 300° - 305° C (Found: C, 70.12; H, 6.30; N, 7.12; C12H13NO2 requires; C, 70.92; H, 6.45; N, 6.89%).

Workup

  1. temperaturethe mixture was refluxed for 4 hrs
  2. temperatureAfter cooling the dark solution
  3. additionwas poured
  4. customonto crushed ice
  5. filtrationfiltered
  6. customseparated as a white solid, m.p. (EtOH) 300° - 305° C (Found: C, 70.12; H, 6.30; N, 7.12; C12H13NO2 requires; C, 70.92; H, 6.45; N, 6.89%)

Sources & evidence

ORD record
ord-f1b028b7cf7344529babdca46b6d072a
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

Loading…