Acetic Acid → N-(3-formyl-2-methylphenyl)acetamide

HRID 326113Notes

Reaction equation

HRID 326113 reaction equation
[CH3:1][C:2]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#N.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(O)(=[O:20])C>>[CH3:1][C:2]1[C:9]([NH:10][C:11](=[O:13])[CH3:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:20]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 2548423-Amino-2-methylbenzonitrile

Product 1

HCID 20462526N-(3-formyl-2-methylphenyl)acetamide

Procedure

39 g (0.3 mole) of 2-methyl-3-amino-benzonitrile were dissolved in 75 ml of acetic acid, 30 ml (0.3 mole) of acetic anhydride were added, the mixture was heated with reflux for 5 minutes, and cooled. The solid obtained was filtered off an the evaporation of the solvent furnished an additional quantity of solid which was added to the preceding one. After recrystallisation of the whole from toluene, 44 g (95%) of colourless flakes were obtained, with a melting point of 160° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 5 minutes
  3. temperaturecooled
  4. customThe solid obtained
  5. filtrationwas filtered off an
  6. customthe evaporation of the solvent
  7. customfurnished an additional quantity of solid which
  8. additionwas added to the preceding one
  9. customAfter recrystallisation of the whole from toluene, 44 g (95%) of colourless flakes
  10. customwere obtained, with a melting point of 160° C.

Sources & evidence

ORD record
ord-d739e76f6b5e48e680805541cff11c6f
Source dataset
uspto-grants-1984_04
Patent number
US04444776

Reaction notes

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