Hydrochloric Acid → 3-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide

HRID 1452931

Reaction equation

HRID 1452931 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)([O-])=O>C(O)C.O.[Fe]>[NH2:2][C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 225673203-nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide

Product 1

HCID 225673553-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamideYield 46.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

3-Amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide can be obtained in the following way: 0.06 ml of an aqueous hydrochloric acid solution is added to a solution of 0.28 g of 3-nitro-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide in 15 ml of absolute ethanol and 0.3 ml of water. The reaction mixture is refluxed, then 0.12 g of powdered iron is added in small portions. The reaction mixture is refluxed for 2 hours and is then cooled to a temperature in the region of 20° C. 30 ml of water are added to the mixture, which is filtered through Celite®, and the solid is washed with water then ethyl acetate. The filtrate is basified with an aqueous 32% ammonium hydroxide solution to a pH in the region of 12, and is then extracted with 3 times 20 ml of ethyl acetate. The organic extracts are pooled, washed with 3 times 10 ml of water, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The solid residue is washed successively with diisopropyl ether then dichloromethane, partially dried and dried. 0.12 g of 3-amino-N-(3-phenyl-1H-indazol-5-yl)benzenesulfonamide is thus obtained in the form of an off-white powder melting at 205° C.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. temperatureThe reaction mixture is refluxed for 2 hours
  3. filtrationis filtered through Celite®
  4. washthe solid is washed with water
  5. extractionis then extracted with 3 times 20 ml of ethyl acetate
  6. washwashed with 3 times 10 ml of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  10. washThe solid residue is washed successively with diisopropyl ether
  11. dry with materialdichloromethane, partially dried
  12. customdried

Sources & evidence

ORD record
ord-c5cb3f720de74c40823ada5662142b05
Source dataset
uspto-grants-2009_01
Patent number
US07473701B2

Linked notes

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