N-methyl-4-(4-morpholinyl)-3-nitrobenzenesulfonamide → 3-amino-N-methyl-4-(4-morpholinyl)benzenesulfonamide

HRID 536044Notes

Reaction equation

HRID 536044 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:8]([N+:18]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>C1COCC1.[Pd]>[NH2:18][C:8]1[CH:7]=[C:6]([S:3]([NH:2][CH3:1])(=[O:4])=[O:5])[CH:11]=[CH:10][C:9]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 9279191N-methyl-4-(4-morpholinyl)-3-nitrobenzenesulfonamide

Product 1

HCID 433827823-amino-N-methyl-4-(4-morpholinyl)benzenesulfonamideYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N-methyl-4-(4-morpholinyl)-3-nitrobenzenesulfonamide (2.5 g, 8.30 mmol) in THF (100 mL) under nitrogen, Pd/C (0.8 g) was added. The flask was then evacuated and recharged with hydrogen three times. The resulting mixture was allowed to stir under a hydrogen atmosphere at 50° C. overnight. The mixture was then filtered and concentrated to afford 3-amino-N-methyl-4-(4-morpholinyl)benzenesulfonamide (1.98 g, 88%). 1H NMR (400 MHz, DMSO-d6) δ 7.07-7.17 (m, 2H), 7.01 (d, J=8.28 Hz, 1H), 6.94 (dd, J=1.88, 8.16 Hz, 1H), 5.20 (s, 2H), 3.72-3.81 (m, 4H), 2.80-2.89 (m, 4H), 2.38 (d, J=4.77 Hz, 3H); MS (m/z) 272.2 (M+H+)

Workup

  1. customThe flask was then evacuated
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86f42d0c62c14f5d8618a20d161632a4
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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