2-Chloro-4-fluoro-5-nitro-thiolbenzoic acid (methoxycarbonylmethyl) ester → 5-Amino-2-chloro-4-fluoro-thiolbenzoic acid (methoxycarbonylmethyl) ester

HRID 846014Notes

Reaction equation

HRID 846014 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:24])[C:8]1[C:13]([C:14]2([Cl:23])[CH2:18][C:17]([F:19])=[C:16]([N+:20]([O-])=O)[S:15]2)=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[H][H]>O1CCCC1.[Ni]>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:24])[C:8]1[C:13]([C:14]2([Cl:23])[CH2:18][C:17]([F:19])=[C:16]([NH2:20])[S:15]2)=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 867460242-Chloro-4-fluoro-5-nitro-thiolbenzoic acid (methoxycarbonylmethyl) esterHCID 178418361HCID 178418361, compound

Product 1

HCID 867460235-Amino-2-chloro-4-fluoro-thiolbenzoic acid (methoxycarbonylmethyl) esterYield 89.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10.4 g of the 2-chloro-4-fluoro-5-nitro-thiolbenzoic acid (methoxycarbonylmethyl) ester obtained in accordance with Example P1 are hydrogenated with hydrogen under normal pressure in 150 ml of tetrahydrofuran at a temperature of 20°-25° C. in the presence of 2 g of Raney nickel catalyst. After the stoichiometric amount of hydrogen has been consumed, the catalyst is separated off and the solution is concentrated by evaporation, yielding 8.6 g of 5-amino-2-chloro-4-fluoro-thiolbenzoic acid (methoxycarbonylmethyl) ester having a melting point of from +88° to +89° C.

Workup

  1. customAfter 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-334227dc4b81461d81f05cae651c74e5
Source dataset
uspto-grants-1992_08
Patent number
US05135562

Reaction notes

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