HCID 20229120, compound → 5-Amino-2-(1-pyrrolidinyl)benzenesulfonic acid

HRID 1833303Notes

Reaction equation

HRID 1833303 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([S:10]([OH:13])(=[O:12])=[O:11])[CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([S:10]([OH:13])(=[O:11])=[O:12])[CH:9]=1

Participants

4

Reactant 1

HCID 20229120HCID 20229120, compound

Product 1

HCID 213887455-Amino-2-(1-pyrrolidinyl)benzenesulfonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

72.4 Grams 2-chloro-5-nitrobenzenesulfonic acid was added in portions to 134 ml pyrrolidine, while keeping the temperature below 65° C. After the addition, the reaction was heated at reflux temperature with stirring for 7 hours and allowed to stand overnight at room temperature. The reaction was poured into 800 ml ice water and the solution made strongly acidic with concentrated HCl until light yellow crystals separated. The product was filtered, washed with a little dilute HCl and the moist cake was recrystallized from about 800 ml water to give 70.7 grams 5-nitro-2-pyrrolidinylbenzenesulfonic acid. m.p. = 178°-179° C. The nitro compound was reduced catalytically in ethanol with 5% palladium on carbon catalyst to give 5-amino-2-pyrrolidinyl-benzenesulfonic acid. m.p. = 255°-256° C.

Sources & evidence

ORD record
ord-32582ac3bfef4c92872add68f9ace61f
Source dataset
uspto-grants-1978_01
Patent number
US04066457

Reaction notes

Loading…