4-[4-[2-(Acetylamino)propyl]phenyl]-4-oxobutanoic acid → 4-[4-[2-(Acetylamino)propyl]phenyl]butanoic acid

HRID 1065205Notes

Reaction equation

HRID 1065205 reaction equation
[C:1]([NH:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([NH:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 128502534-[4-[2-(Acetylamino)propyl]phenyl]-4-oxobutanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 128502544-[4-[2-(Acetylamino)propyl]phenyl]butanoic acidYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Four and two-tenths g (0.015 moles) of 4-[4-[2-(Acetylamino)propyl]phenyl]-4-oxobutanoic acid was shaken under fifty lb/in2 of hydrogen pressure in 200 ml of acetic acid in the presence of one gram of 10% Pd/C in a Parr apparatus. Reduction was complete in approximately 1.25 hours. After removal of the catalyst by filtration, the solvent was distilled in the rotary evaporator leaving 3.8 g of a colorless syrup. An aliquot of the syrup was rubbed under acetonitrile whereupon it crystallized. Recrystallization from acetonitrile yielded white crystals of mp 114°-117°.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. distillationthe solvent was distilled in the rotary evaporator

Sources & evidence

ORD record
ord-eb6ea4af7245498fab44bc3a980c5aa1
Source dataset
uspto-grants-1982_05
Patent number
US04329281

Reaction notes

Loading…