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

HRID 48160Notes

Reaction equation

HRID 48160 reaction equation
[Cl:1][C:2]1[C:3]([CH3:22])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:21])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1)[CH3:10]>[Pt].CN(C)C=O>[Cl:1][C:2]1[C:3]([CH3:22])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:21])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)[CH3:10]

Participants

4

Reactant 1

HCID 22742105N-(chloro-3-methylisothiazol-5-yl)-2-(4-hydroxy-3-nitrophenyl)propionamide

Product 1

HCID 22742099N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

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.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6f5b30c397754a228cb0e5f413cb3503
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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