2-Nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester → 2-Amino-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069270Notes

Reaction equation

HRID 2069270 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[N+:20]([O-])=O>C(O)C.[Ni]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[C:7]([C:16]([F:17])([F:18])[F:19])=[CH:6][C:5]=1[NH2:20]

Participants

4

Reactant 1

HCID 589645312-Nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589645242-Amino-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl esterYield 84.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

300 mg of 2-nitro-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester in 10 ml of dry ethanol are hydrogenated in presence of 60 mg of Raney nickel, After filtration of the catalyst the solution is evaporated to dryness yielding 233 mg of 2-amino-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester as yellow powder, m.p. 85-117° C. (decomp.).

Workup

  1. filtrationAfter filtration of the catalyst the solution
  2. customis evaporated to dryness

Sources & evidence

ORD record
ord-991edd439a7e471bbb5257abb2cef030
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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