Ethyl 4-(4-nitrophenylsulfonyl)butanoate → Ethyl 4-(4-aminophenylsulfonyl)butanoate

HRID 1946703Notes

Reaction equation

HRID 1946703 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 59446990Ethyl 4-(4-nitrophenylsulfonyl)butanoate2×

Product 1

HCID 59446984Ethyl 4-(4-aminophenylsulfonyl)butanoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 4-(4-nitrophenylsulfonyl)butanoate (Intermediate 47, 4.5 g; 14.9 mmol) in ethanol (200 ml) was treated with palladium (450 mg, 5% on C). The mixture was stirred under hydrogen for 18 hours, filtered and the solvent removed in vacuo to give the title compound as an off-white solid (4.0 g, quant).

Workup

  1. filtrationfiltered
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-bb81b7beb8f449bf8643989d6a333557
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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