Ethyl 3-(4-nitrophenyl)-2-propenoate → Ethyl 3-(4-aminophenyl)propanoate

HRID 54981Notes

Reaction equation

HRID 54981 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateHCID 2723923Ammonium formate

Product 1

HCID 10442595Ethyl 3-(4-aminophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product was made by reducing ethyl 4-nitrocinnamate (110.6 g, 0.5 mol) with 10% palladium on Carbon (4.0 g) in 95% ethanol (2 L) in the presence of ammonium formate (126 g) to afford ethyl 3-(4-aminophenyl)propionate which was sulfonated with methanesulfonyl chloride in CH2Cl2 in the presence of pyridine to produce 102 g (75.2%) of N-[4-(ethoxycarbonylethyl)phenyl]methanesulfonamide.

Sources & evidence

ORD record
ord-9c407937a69a44a9adfc9992917e0aec
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

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