Reaction #76438

Reaction equation

N-(chloro-3-methylisothiazol-5-yl)-2-(4-hydroxy-3-nitrophenyl)propionamide

→

N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide

Yield 89.6%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration
2. 2
   Otherthe filtrate evaporated in vacuo

Procedure

A mixture of N-(chloro-3-methylisothiazol-5-yl)-2-(4-hydroxy-3-nitrophenyl)propionamide (11.0 g, 0.0322 mol) and 3% platinum on carbon in N,N-dimethylformamide (100 ml) was hydrogenated at 15 bar (15×105 Nm−2) for 6 hours at room temperature. The catalyst was removed by filtration and the filtrate evaporated in vacuo to give N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide (9.0 g) as an off-white solid, m.p.222-223° C.

Source