O-Toluidine → 3-Methyl-N-(2-methylphenyl)but-2-enamide

HRID 1198948Notes

Reaction equation

HRID 1198948 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[CH3:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11]>N1C=CC=CC=1>[O:5]=[C:4]([NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[CH3:8])[CH:3]=[C:2]([CH3:7])[CH3:1]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 191774333-Methyl-N-(2-methylphenyl)but-2-enamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methylbut-2-en-oylchloride (24.2 g) was added dropwise to a stirred solution of 2-methylaniline (20 g) in anhydrous pyridine (200 cm3) cooled to 0°. After 1 hour solvent was evaporated in vacuo to yield a solid which was recrystallised from ether/petroleum ether (boiling range 40-60) to afford the title compound, m.p. 105 (29.5 g).

Workup

  1. temperaturecooled to 0°
  2. customAfter 1 hour solvent was evaporated in vacuo
  3. customto yield a solid which
  4. customwas recrystallised from ether/petroleum ether (boiling range 40-60)

Sources & evidence

ORD record
ord-75b2d942296f4a8e86311197647a3f77
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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