2-Chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) ester → 5-Amino-2-chloro-4-fluorothiobenzoic acid (methoxycarbonylmethyl) ester

HRID 1033215Notes

Reaction equation

HRID 1033215 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[S:19])[C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([F:17])=[CH:10][C:9]=1[Cl:18])=[O:4].[H][H]>O1CCCC1.[Ni]>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[S:19])[C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([F:17])=[CH:10][C:9]=1[Cl:18])=[O:4]

Participants

5

Reactant 2

HCID 540569242-Chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) esterHCID 178418361HCID 178418361, compound

Product 1

HCID 539902175-Amino-2-chloro-4-fluorothiobenzoic acid (methoxycarbonylmethyl) esterYield 91.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10.4 g of the resulting 2-chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) ester are hydrogenated with hydrogen under normal pressure in 150 ml of tetrahydrofuran at a temperature of from 20° to 25° C. in the presence of 2 g of Raney nickel catalyst. When the stoichiometric amount of hydrogen has been consumed, the catalyst is separated off and the solution is concentrated by evaporation to yield 8.6 g of 5-amino-2-chloro-4-fluorothiobenzoic acid (methoxycarbonylmethyl) ester having a melting point of from +88° to +89° C.

Workup

  1. customWhen the stoichiometric amount of hydrogen has been consumed
  2. customthe catalyst is separated off
  3. concentrationthe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-211d75b6286241d49ff602ad66f9a45a
Source dataset
uspto-grants-1994_05
Patent number
US05310722

Reaction notes

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