ChemicalBook CAS DataBase List 2-methyl-N-(4-nitrophenyl)propanamide

2-methyl-N-(4-nitrophenyl)propanamide synthesis

4synthesis methods

Product Name:2-methyl-N-(4-nitrophenyl)propanamide
CAS Number:7160-11-4
Molecular formula:C10H12N2O3
Molecular Weight:208.21

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79-30-1 Synthesis

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7160-11-4
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Yield:7160-11-4 1.8 g

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 0.5 h;

Steps:

Z.1 Step 1: N-(4-nitrophenyl)isobutyramide

To a stirred solution of an isobutyric acid (1.2 g, 0.0136 mol) in dry diethylether (10 mL) at 0°C, thionyl chloride (8 mL) was added and the mixture was heated at 85°C for 1.2 h. After completion of the reaction, excess of thionyl chloride was removed under reduced pressure and the crude product obtained was dissolved in DCM (10 mL) and a mixture of p-nitroaniline (2.06 g, 0.014 mol) and triethylamine (4.5 mL) in DCM (10 mL) was added and stirred for 30 min at rt. After completion of starting material on TLC, the mixture was quenched with ice and poured into ice cold water. The aqueous layer was extracted with ethyl acetate (3 x 250 mL). The organic layer was washed with water (3 x 100 mL), dried over Na₂S0₄ and concentrated to obtain crude material which was triturated with pentane to obtain N-(4-nitrophenyl)isobutyramide (1.8 g, 64.2%) as brown solid. 1H NMR (400 MHz, DMSO-d₆): δ 10.46 (s, 1H), 8.21 (s, 2H), 7.84 (s, 2 H), 1.12 (s, 6H).

References:

WO2015/38417,2015,A1 Location in patent:Page/Page column 125; 126