HCID 18613617, compound → N-(4-chloro-3-methyl-5-isothiazolyl)-3-amino-4-hydroxyphenylacetamide

HRID 1264620Notes

Reaction equation

HRID 1264620 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-])=O)[CH:11]=1>[Pt].CN(C)C=O>[Cl:1][C:2]1[C:3]([CH3:21])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH2:17])[CH:11]=1

Participants

4

Reactant 1

HCID 18613617HCID 18613617, compound

Product 1

HCID 18613611N-(4-chloro-3-methyl-5-isothiazolyl)-3-amino-4-hydroxyphenylacetamideYield 79%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

N-(4-Chloro-3-methyl-5-isothiazolyl)-4-hydroxy-3-nitrophenylacetamide (374 g, 0.114 mol) was hydrogenated at 15 bar over a 3% w/w platinum on carbon catalyst (15 g) in N,N-dimethylformamide (180 ml). Once the reduction was complete, the catalyst was removed by filtration and the filtrate was evaporated in vacuo to give N-(4-chloro-3-methyl-5-isothiazolyl)-3-amino-4-hydroxyphenylacetamide (26.8 g) as a pale brown solid, which used without further purification in the next step.

Workup

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

Sources & evidence

ORD record
ord-0486c87193f9411c96d14e01a2752f20
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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