4-Methoxy-2-methylbenzamide synthesis
- Product Name:4-Methoxy-2-methylbenzamide
- CAS Number:139583-91-8
- Molecular formula:C9H11NO2
- Molecular Weight:165.19
31310-08-4
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Yield:-
Reaction Conditions:
with ammonia in tetrahydrofuran;water at 30; for 0.25 h;
Steps:
83.B
[00304] A mixture of 83A (386.05 g) in dichloromethane (3 L) was combined in a flask equipped with a mechanical stirrer, reflux condenser and addition funnel to provide a very thick slurry. DMF (1 mL) was added as catalyst, followed by oxalyl chloride (330 g) dropwise over about 2 h. The acidic effluent gasses were scrubbed through a K2CO3 scrubber. The slurry slowly dissolved during the addition to provide a red solution of acid chloride. Dichloromethane (1.3 L) was distilled off at 3O0C with slight vacuum, and the resulting concentrated solution of acid chloride was polish filtered through a course sintered glass funnel to remove some insoluble matter. This filtered solution was concentrated to a crystalline residue and pumped down under high vacuum for 30 min to remove any excess oxalyl chloride. The crystalline residue was dissolved in THF (550 mL) and titrated into a large flask containing ice cold concentrated ammonium hydroxide (1 L) over ~15 min. The temperature quickly rose to ~30°C with the formation of a thick slurry of product. To this oily slurry of product, water (3 L) was added over ~15 min to provide a thick white slurry of product. This product was filtered over course sintered glass and washed with water (1.5 L) and dried under nitrogen/ vacuum for 36 h. 367.8g of 83B was isolated as an off-white solid. HPLC showed a peak at the expected retention time of 11.85 min, with a purity of 95.15% at 220nm, and 97.29% at 254 nm.
References:
WO2006/76246,2006,A2 Location in patent:Page/Page column 148
6245-57-4
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