Methanol → N-(2-Methylphenyl)butanimidic acid

HRID 1168003Notes

Reaction equation

HRID 1168003 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:13])[CH2:10][CH2:11][CH3:12].CO>C1(C)C=CC=CC=1>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:9](=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 7242O-ToluidineHCID 8855Butyryl chloride

Product 1

HCID 221809N-(2-Methylphenyl)butanimidic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

1128.6 g of o-toluidine were initially charged in 500 ml of toluene and heated to 90° C. 134.3 g of butyryl chloride were added dropwise within 2 hours. After completed addition, the mixture was heated to reflux and stirring continued at this temperature until the end of gas formation. The mixture was cooled to 70° C., 12 ml of methanol were added and stirring was continued for an hour. To remove the methanol, the mixture was heated and 70 ml were distilled off. 300 ml of toluene were then distilled off and 400 ml of cyclohexane were added. The mixture was cooled to 10° C. and filtration gave 199.5 g (92% yield) of the product in 98% purity after drying.

Workup

  1. additionaddition
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. temperatureThe mixture was cooled to 70° C.
  5. stirringstirring
  6. waitwas continued for an hour
  7. customTo remove the methanol
  8. temperaturethe mixture was heated
  9. distillation70 ml were distilled off
  10. distillation300 ml of toluene were then distilled off
  11. addition400 ml of cyclohexane were added
  12. temperatureThe mixture was cooled to 10° C.
  13. filtrationfiltration

Sources & evidence

ORD record
ord-e73b5b86e610472dba0d7db5bf73728e
Source dataset
uspto-grants-2003_09
Patent number
US06620962B2

Reaction notes

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