Hydrazine hydrate (1:1) → 4-amino-N-methylbenzene-1-sulfonamide

HRID 407290Notes

Reaction equation

HRID 407290 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N-:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866087554-Nitrobenzenesulfonyl methylamide

Product 1

HCID 743684-amino-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of the crude 4-nitrobenzenesulfonyl methylamide prepared above in 45 mL of ethanol, was added a 1 mL slurry of Raney Nickel. Hydrazine monohydrate (18 mmol) was added slowly in several portions. A change in the solution colour from yellow to colourless indicated the reaction was complete. The mixture was stirred for an additional 1 hr. The solids were removed by filtration and the solvent was evaporated. The resulting crude material was purified by flash column chromatography eluting with CH2Cl2:MeOH=10:1 to yield 2.09 g (90% for two steps) of the title compound as a pale orange powder.

Workup

  1. customThe solids were removed by filtration
  2. customthe solvent was evaporated
  3. customThe resulting crude material was purified by flash column chromatography
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-7e8183e1822740b99ac5bcbd14cd72b6
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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