[2-(2-Nitro-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester → [2-(2-Amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580395Notes

Reaction equation

HRID 580395 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH2:14][CH:15]([CH:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:12])([F:13])[F:11])=[CH:6][C:5]=1[CH2:14][CH:15]([CH:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14156190[2-(2-Nitro-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 14156191[2-(2-Amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 25.0 g (0.055 mol) of [2-(2-nitro-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (see Example 4A) in 200 ml of methanol was treated with a cold suspension of 2.5 g of 5% palladium on charcoal in 50 ml of methanol (under nitrogen) and placed on the Parr apparatus at 58 lbs. of hydrogen. The theoretical amount of hydrogen was consumed in about 30 minutes and this mixture was then heated at 50°-55° C. for one hour to assure that all of the nitro compound had dissolved. The mixture was removed from the Parr and allowed to stand at room temperature overni-ght. The flask was heated to dissolve the crystallized product, and the hot solution was filtered through Celite (under nitrogen) and washed with hot methanol. The colorless filtrate was concentrated on a rotary evaporator to give 22.2 g of a nearly colorless solid. The latter was triturated with 100 ml of hexane and then with 50 ml of hexane. The solvent was decanted and the entrained solvent removed on a rotary evaporator to give 21.3 g of product, melting point 124°-127° C. A sample of this material, after crystallization from methanol, melted at 125°-127° C.

Workup

  1. customThe theoretical amount of hydrogen was consumed in about 30 minutes
  2. temperaturethis mixture was then heated at 50°-55° C. for one hour
  3. dissolutionhad dissolved
  4. customThe mixture was removed from the Parr
  5. customto stand at room temperature
  6. temperatureThe flask was heated
  7. dissolutionto dissolve the crystallized product
  8. filtrationthe hot solution was filtered through Celite (under nitrogen)
  9. washwashed with hot methanol
  10. concentrationThe colorless filtrate was concentrated on a rotary evaporator
  11. customto give 22.2 g of a nearly colorless solid
  12. customThe latter was triturated with 100 ml of hexane
  13. customThe solvent was decanted
  14. customthe entrained solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-523d7966cb5445e38f9bced2848f4a13
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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