Ammonium formate → 2-Methoxy-4-phenylsulphonylaniline

HRID 841197Notes

Reaction equation

HRID 841197 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:10]=[CH:9][C:8]=1[N+:22]([O-])=O>O.[Pd].CO.C(OCC)(=O)C>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([S:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:14])=[O:15])[CH:10]=[CH:9][C:8]=1[NH2:22]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 226212362-Methoxy-4-phenylsulphonylnitrobenzene

Product 1

HCID 226212722-Methoxy-4-phenylsulphonylaniline

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ammonium formate (0.1 83 g) in water (2.5 ml) was added to a mixture of 10% palladium on carbon (0.03 g) and 2-methoxy-4-phenylsulphonylnitrobenzene (Method 22) (0.213 g) in methanol (10 ml) and ethyl acetate (1 ml). The mixture was heated and stirred under reflux under argon for 4 hours then cooled and filtered through diatomaceous earth. The filter was washed with ethyl acetate (2×5 ml) and the filtrates were combined. The solution was concentrated by evaporation to approximately 2 ml and the resultant solid was collected, washed with water (2×5 ml) and dried in vacuo to give the title compound as a solid. M.p.149-150.5° C.; NMR: 3.8 (s, 3H), 5.78 (s, 2H), 6.67 (d, 1H), 7.17 (s, 1H), 7.26 (dd, 1H), 7.5-7.62 (m, 3H), 7.84 (d, 2H); MS: 262 (M−H)−; EA: C13H13NO3S requires C, 59.3; H, 5.0; N, 5.3; S, 12.2%; found: C, 59.1; H, 4.9; N, 5.2; S, 12.2%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux under argon for 4 hours
  3. temperaturethen cooled
  4. filtrationfiltered through diatomaceous earth
  5. washThe filter was washed with ethyl acetate (2×5 ml)
  6. concentrationThe solution was concentrated by evaporation to approximately 2 ml
  7. customthe resultant solid was collected
  8. washwashed with water (2×5 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-4be6240b639b41f9ae748a599e58f600
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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