1-Amino-2-(4-chlorophenylazo)-naphthalene-5-sulfonamide → 1-Naphthalenesulfonamide, 5,6-diamino-
Reaction equation
[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([NH2:15])(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[N:16]=NC1C=CC(Cl)=CC=1>Cl>[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([NH2:15])(=[O:13])=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:16]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 18,1 g (80 mmol) stannous chloride dihydrate in 100 ml concentrated hydrochloric acid was added 10,0 g (27,7 mmol) 1-amino-2-(4-chlorophenylazo)-naphthalene-5-sulphonamide. The mixture was stirred at 70° C. for 3 h. After cooling to 25° C., the mixture was poured into 200 ml ice-water. The precipitate was filtered off and washed with 4N hydrochloric acid. The crude product was stirred with ice-water. The precipitate was filtered off and washed with ice-water and ethanol to give 6,7 g 1,2-diamino-naphthalene-5-sulphonamide as a hydrochloride salt.
Workup
- temperatureAfter cooling to 25° C.
- filtrationThe precipitate was filtered off
- washwashed with 4N hydrochloric acid
- stirringThe crude product was stirred with ice-water
- filtrationThe precipitate was filtered off
- washwashed with ice-water and ethanol
Sources & evidence
- ORD record
- ord-096ef5aee9de4f5a90ca4b1a48f53af0
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889855
Reaction notes
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