[1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid, dimethyl ester → [2-(2-Amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 1253305Notes

Reaction equation

HRID 1253305 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[C:8]([CH2:9][CH:10]([CH:19]([C:24]([O:26][CH3:27])=[O:25])[C:20]([O:22][CH3:23])=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:7]([N+:28]([O-])=O)[CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C.CCCCCC>[F:1][C:2]([F:31])([F:32])[C:3]1[C:8]([CH2:9][CH:10]([CH:19]([C:24]([O:26][CH3:27])=[O:25])[C:20]([O:22][CH3:23])=[O:21])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[C:7]([NH2:28])[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 14156192[1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 14156193[2-(2-Amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Catalytic reduction of 40.4 g (0.088 mol) of [2-(6-trifluoromethyl-2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (in two portions) following the procedure of Example 28 part B gave 36.9 g of nearly colorless solid, melting point 111°-113° C. Rf 0.62 (1:1 ethyl acetate-hexane). A sample crystallized from methanol melted at 112°-114° C.

Workup

  1. customgave 36.9 g of nearly colorless solid, melting point 111°-113° C
  2. customA sample crystallized from methanol melted at 112°-114° C.

Sources & evidence

ORD record
ord-cbd54cccd7dd43bb847d324d38b07bd4
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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