N-(4-Nitrobenzoyl)-beta-alanine → N-(4-Aminobenzoyl)-beta-alanine

HRID 1648730

Reaction equation

HRID 1648730 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 591374N-(4-Nitrobenzoyl)-beta-alanineHCID 178418361HCID 178418361, compound

Product 1

HCID 719629N-(4-Aminobenzoyl)-beta-alanine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 15 g. finely powdered 4-nitrobenzoyl-β-alanine in 200 ml. ethanol was stirred in an atmosphere of hydrogen in the presence of 1 g. of palladium-charcoal (5%), while cooling gently. When the absorption of hydrogen had ceased, the reaction mixture was filtered and the filtrate concentrated to a small volume. Upon adding diethyl ether and cooling, 4-aminobenzoyl-β-alanine was obtained. The yield was 11.5 g.; m.p. 156°-158° C.

Workup

  1. additionA suspension of 15 g
  2. customWhen the absorption of hydrogen
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate concentrated to a small volume
  5. additionUpon adding diethyl ether
  6. temperaturecooling

Sources & evidence

ORD record
ord-5d0d7d473fa1422ba7376a1e74cf250c
Source dataset
uspto-grants-1983_11
Patent number
US04412992

Linked notes

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