4-(2-Nitrophenyl)-2-phthalimidobutyric acid → 4-(2-Aminophenyl)-2-phthalimidobutyric acid

HRID 1194975Notes

Reaction equation

HRID 1194975 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26])[C:13]([OH:15])=[O:14])([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 144072514-(2-Nitrophenyl)-2-phthalimidobutyric acid

Product 1

HCID 140106814-(2-Aminophenyl)-2-phthalimidobutyric acidYield 84.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 300 ml of methanol, 13 g of 4-(2-nitrophenyl)-2-phthalimidobutyric acid is catalytically reduced at ambient temperature and under atmospheric pressure with use of 3 g of 5% palladium-carbon as a catalyst. After the calculated amount of hydrogen is absorbed, the insoluble material is separated by filtration, and washed four times with 300 ml of acetone. The acetone washings and the methanol portion are combined and concentrated under reduced pressure. The residue is admixed with 50 ml of ethanol, and the crystals which separate out are collected by filtration to give 10.1 g of 4-(2-aminophenyl)-2-phthalimidobutyric acid as yellow prisms. m.p. 198°-203° C. (decomp.).

Workup

  1. customAfter the calculated amount of hydrogen is absorbed
  2. customthe insoluble material is separated by filtration
  3. washwashed four times with 300 ml of acetone
  4. concentrationconcentrated under reduced pressure
  5. customthe crystals which separate out
  6. filtrationare collected by filtration

Sources & evidence

ORD record
ord-93da323a9f3c499d9d18e67d7cad04aa
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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