Acetic Acid → 3-(2-Aminobenzene-1-sulfonyl)-4-chlorobenzoic acid

HRID 1447561Notes

Reaction equation

HRID 1447561 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)(=[O:13])=[O:12].Cl.C(O)(=O)C>O>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[Cl:1])[C:6]([OH:8])=[O:7])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 203841844-Chloro-3-(2-nitrobenzene-1-sulfonyl)benzoic acid

Product 1

HCID 203841823-(2-Aminobenzene-1-sulfonyl)-4-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-3-(o-nitrophenylsulphonyl)benzoic acid (1.71 g), stannous chloride (3.12 g ), concentrated hydrochloric acid (6.6 ml) and acetic acid (25 ml) was heated on the steam bath for 30 min., cooled, and diluted with water. 3-(o-Aminophenylsulphonyl)-4-chlorobenzoic acid was filtered off, washed with water and dried, m.p. 235°-238° C., providing on recrystallisation from acetic acid, m.p. 246°-248° C.

Workup

  1. temperaturewas heated on the steam bath for 30 min.
  2. temperaturecooled
  3. filtration3-(o-Aminophenylsulphonyl)-4-chlorobenzoic acid was filtered off
  4. washwashed with water
  5. customdried
  6. customm.p. 235°-238° C., providing on recrystallisation from acetic acid, m.p. 246°-248° C.

Sources & evidence

ORD record
ord-5aee2d601e6747f79bea7d419bd31903
Source dataset
uspto-grants-1979_12
Patent number
US04177257

Reaction notes

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