4-Nitrobenzoic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide → Methyl N-(4-aminobenzoyl)-N-phenyl-beta-alaninate

HRID 50375Notes

Reaction equation

HRID 50375 reaction equation
[C:1]1([N:7]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].C(Cl)Cl.C(O)C>CO.[Pd]>[C:1]1([N:7]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 184123414-Nitrobenzoic acid-n-phenyl-n-(2-methoxycarbonylethyl)amideHCID 21584144Dichloromethane ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18412585Methyl N-(4-aminobenzoyl)-N-phenyl-beta-alaninate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

22 g (67 mmol) of 4-nitrobenzoic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide were hydrogenated in 500 mL of methanol with 2 g of 10% palladium on charcoal at 3 bar hydrogen pressure for 3 hours. After filtration and distillation of the solvent, the reaction mixture was washed with 100 mL of ether and the white crystalline product was further reacted directly. Yield: 18.6 g (94% of theory), Rf value: 0.70 (silica gel; methylene chloride/ethanol=19:1).

Workup

  1. filtrationAfter filtration and distillation of the solvent
  2. washthe reaction mixture was washed with 100 mL of ether
  3. customthe white crystalline product was further reacted directly

Sources & evidence

ORD record
ord-9448e0cb7ec0459f90db984743ddf7f6
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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