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Hydrochloric Acid → N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

HRID 25408
Notes
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Reaction equation

HRID 25408 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=2)[NH:12][N:11]=1)([O-])=O.C(O)C.Cl>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:22])=[O:21])[CH:17]=2)[NH:12][N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22567362N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

Product 1

HCID 22567188N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamideYield 15.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 962WaterSolvent

Procedure

N-[3-(2-Aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: 59 mg of powdered iron are added in small fractions to a solution, at reflux, of 280 mg of N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide, 10 ml of ethanol, 82 μl of distilled water and 51 μl of 12 N hydrochloric acid, and the reaction medium is then brought to reflux for 3 hours. After returning to a temperature in the region of 20° C., the suspension is filtered, and washed with ethanol. The filtrate is diluted with water and brought to a pH in the region of 10 with a 1 N sodium hydroxide solution. The filtrate is extracted with ethyl acetate and the remaining insoluble material is removed by filtration. The organic phase is washed with distilled water, dried with magnesium sulfate, treated with 3S black, filtered and concentrated to dryness under reduced pressure. The foam thus obtained is triturated with diisopropyl ether, filtered and dried. 40 mg of N-[3-(2-aminophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a white amorphous solid solvated with 1 mol of diisopropyl ether (analysis C20H18N4O4S2C6H14O % calculated C, 57.33; H, 5.92; N, 10.29; O, 14.69; S, 11.77. % found C, 57.41; H, 5.96; N, 10.01; S, 11.26).

Workup

  1. temperatureto reflux for 3 hours
  2. customAfter returning to a temperature in the region of 20° C.
  3. filtrationthe suspension is filtered
  4. washwashed with ethanol
  5. additionThe filtrate is diluted with water
  6. extractionThe filtrate is extracted with ethyl acetate
  7. customthe remaining insoluble material is removed by filtration
  8. washThe organic phase is washed with distilled water
  9. dry with materialdried with magnesium sulfate
  10. additiontreated with 3S black
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure
  13. customThe foam thus obtained
  14. customis triturated with diisopropyl ether
  15. filtrationfiltered
  16. customdried

Sources & evidence

ORD record
ord-f11bd1193c6b4ea793f8452b7af0ac3a
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858638B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes