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

HRID 1031814Notes

Reaction equation

HRID 1031814 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 ethaniol, 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-a57a2a8f53134ba7a1e9bf725a729056
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

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