Ammonium formate → 5-t-butyl-2-methoxy-3-aminophenyl N-t-butyl sulfonamide

HRID 1651476Notes

Reaction equation

HRID 1651476 reaction equation
C([O-])=O.[NH4+].[C:5]([C:9]1[CH:10]=[C:11]([N+:25]([O-])=O)[C:12]([O:23][CH3:24])=[C:13]([S:15]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])=[O:16])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6]>[Pd].CO>[C:5]([C:9]1[CH:10]=[C:11]([NH2:25])[C:12]([O:23][CH3:24])=[C:13]([S:15]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:16])=[O:17])[CH:14]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 150295855-t-butyl-2-methoxy-3-nitrophenyl N-t-butyl sulfonamide

Product 1

HCID 150295865-t-butyl-2-methoxy-3-aminophenyl N-t-butyl sulfonamideYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (8.0 g) was added to a stirred and cooled mixture of 5-t-butyl-2-methoxy-3-nitrophenyl N-t-butyl-sulfonamide (8.0 g) and 10% Palladium on charcoal (1.1 g) in dry methanol (80 ml) under nitrogen. The mixture was stirred at ambient temperature for 1 hour and then filtered through diatomaceous earth. The filtrate was concentrated and taken up into a mixture of ethyl acetate and water. The organic layer was separated and dried over sodium sulphate. After removal of solvent and recrystallization from aqueous ethanol the title compound was obtained as white crystals (6.9 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at ambient temperature for 1 hour
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate was concentrated
  5. additiontaken up into a mixture of ethyl acetate and water
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulphate
  8. customAfter removal of solvent and recrystallization from aqueous ethanol the title compound

Sources & evidence

ORD record
ord-60259e4b53de4df2a0f4a52402df0d5c
Source dataset
uspto-grants-1990_05
Patent number
US04929269

Reaction notes

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