Ammonium Hydroxide → 4-Methyl-2-nitrobenzamide

To a solution of 4-methyl-2-nitrobenzoic acid (1.0 g, 5.52 mmol) in toluene (5 mL) was added oxalyl chloride (1.04 g, 8.28 mmol) at 0° C. and the reaction mixture was stirred at rt for 2 h. Then the reaction mixture was concentrated and the concentrate was dissolved in THF (5 mL). Then NH4OH (1.93 g, 55.20 mmol) was added to the solution at 0-5° C. and the reaction mixture was stirred at rt for 4 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated to afford 1.6 g of the desired product. 1H NMR (300 MHz, DMSO-d6): δ 8.08 (br s, 1H), 7.79 (s, 1H), 7.62 (br s, 1H), 7.57-7.50 (m, 2H), 2.41 (s, 3H).

1. concentrationThen the reaction mixture was concentrated
2. dissolutionthe concentrate was dissolved in THF (5 mL)
3. stirringthe reaction mixture was stirred at rt for 4 h before it
4. customwas quenched with water
5. extractionwas extracted with EtOAc
6. washThe organic layer was washed with brine
7. customseparated
8. customdried
9. filtrationfiltered
10. concentrationconcentrated

ORD 기록

ord-356b990816db44e093bb45f3d85d6216

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09006257B2