Dimethylformamide → 3-(dimethylamino)-N-methoxy-N-methylbenzamide

To a stirred solution of 3-(dimethylamino)benzoic acid (16.5 g, 100 mmol), cooled to 0° C. with a brine/ice bath, was added N,N-dimethylformamide (0.39 mL, 5 mmol) followed by oxalyl chloride (10.5 mL, 120 mmol). The resulting mixture was stirred 4 h at room temperature, until gas evolution stopped and a clear solution was obtained. The mixture was cooled to 0° C. with a brine/ice bath, N,O-Dimethylhydroxylamine (13.7 g, 140 mmol) was added at once, followed by dropwise addition of triethylamine (55.8 mL, 400 mmol) through a dropping funnel, while keeping the internal temperature under 20° C. The resulting suspension was stirred overnight at room temperature, then washed with brine. The aqueous layers were extracted with dichloromethane (2×50 mL), then the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 3-(dimethylamino)-N-methoxy-N-methylbenzamide as an oil [15.5 g, yield 67%; HPLC/MS: m/z=209 (M+H); logP(HCOOH)=0.95].

1. customa clear solution was obtained
2. temperatureThe mixture was cooled to 0° C. with a brine/ice bath
3. customunder 20° C
4. stirringThe resulting suspension was stirred overnight at room temperature
5. washwashed with brine
6. extractionThe aqueous layers were extracted with dichloromethane (2×50 mL)
7. dry with materialthe combined organic layers were dried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-27eed69c55a745f8a3c334cc06c00995

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2