Dimethylformamide → 3,4-Dimethoxyphenylacetamide

Temperature

0 °C

To a solution of 35.31 g (0.18 mole) of (3,4-dimethoxyphenyl)acetic acid in 345 ml of dry toluene and 34.5 ml of dry DMF at 0° C. under argon was added 16.8 ml (0.19 mole) of freshly distilled oxalyl chloride over 40 minutes. The reaction was stirred an additional 35 minutes at 0° C. and then at room temperature for 17 hours. The reaction mixture was again cooled to 0° C. and gaseous ammonia slowly bubbled through it for 1 hour. The reaction mixture was warmed to room temperature and stirred for 4 hours after which the solid was filtered off and partitioned between chloroform and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo giving 20.84 g of the title compound as an off-white solid, mp 142°-144° C.

1. waitat room temperature for 17 hours
2. temperatureThe reaction mixture was again cooled to 0° C.
3. customgaseous ammonia slowly bubbled through it for 1 hour
4. temperatureThe reaction mixture was warmed to room temperature
5. stirringstirred for 4 hours after which the solid
6. filtrationwas filtered off
7. custompartitioned between chloroform and water
8. washThe organic phase was washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. customevaporated in vacuo

ORD record

ord-5103df62c1a149d2ba64cdc95fae6d30

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04742068