5-Ethoxy-1-(4-nitrobenzene-1-sulfonyl)pyrrolidin-2-one → 1-(4-Aminobenzene-1-sulfonyl)-5-ethoxypyrrolidin-2-one

HRID 1761885Notes

Reaction equation

HRID 1761885 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:17]([O:18][CH2:19][CH3:20])[CH2:16][CH2:15][C:14]2=[O:21])(=[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]([N:13]2[CH:17]([O:18][CH2:19][CH3:20])[CH2:16][CH2:15][C:14]2=[O:21])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 30668865-Ethoxy-1-(4-nitrobenzene-1-sulfonyl)pyrrolidin-2-one

Product 1

HCID 30867271-(4-Aminobenzene-1-sulfonyl)-5-ethoxypyrrolidin-2-oneYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At ambient temperature and pressure, 4.5 g of 1-(4-nitrophenylsulphonyl)-5-ethoxypyrrolidin-2-one, dissolved in 200 cm3 of 96° ethanol is hydrogenated in the presence of palladium at 10% on charcoal. The insoluble matter is filtered off and taken up with hot chloroform, filtered, and the last filtrate is added to the alcohol solution resulting from the first filtration. After re-crystallizing the residue twice from 96° ethanol, 2.3 g of the expected product is obtained, m.p. 185°-186° C.

Workup

  1. filtrationThe insoluble matter is filtered off
  2. filtrationfiltered
  3. additionthe last filtrate is added to the alcohol solution
  4. customresulting from the first filtration
  5. customAfter re-crystallizing the residue twice from 96° ethanol

Sources & evidence

ORD record
ord-b50d436338f9439181d9a43259b03393
Source dataset
uspto-grants-1989_05
Patent number
US04829079

Reaction notes

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