Pyridine → alpha-(2-methoxymethylphenyl)-beta-methylacrylic acid-N-methylamide

HRID 36606Notes

Reaction equation

Cl.CN.[CH3:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[CH:17][CH3:18])[C:14](Cl)=[O:15].[N:19]1C=CC=C[CH:20]=1>ClCCl>[CH3:20][NH:19][C:14](=[O:15])[C:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][O:5][CH3:4])=[CH:17][CH3:18]

Participants

Conditions

Temperature: 20 °C

Procedure

1.7 g of methylamine hydrochloride was added to 5.2 g (23 mmol) of α-(2-methoxymethylphenyl)-β-methylacrylic chloride in 30 ml of dichloromethane, and 4 g of pyridine was dripped in at 0° to 5° C. The mixture was stirred for a further 15 hours at about 20° C. The reaction mixture was diluted with 20 ml of dichloromethane and washed with water. The organic phase was dried over sodium sulfate and evaporated down. The crude product was chromatographed on silica gel with methyl tert-butyl ether/cyclohexane (5/1). Removal of the solvent gave 1.5 g (30%) of the title compound in the form of colorless crystals (m.p.: 58° C.).

Workup

customwas dripped in at 0° to 5° C
washwashed with water
dry with materialThe organic phase was dried over sodium sulfate
customevaporated down
customThe crude product was chromatographed on silica gel with methyl tert-butyl ether/cyclohexane (5/1)
customRemoval of the solvent

Sources & evidence

ORD record: ord-89088b4bbe7645989ca3c608b470a08e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416068

Reaction notes

Loading…