4-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide → 3-amino-N-methyl-4-[(1-methylethyl)oxy]benzenesulfonamide

HRID 536041Notes

Reaction equation

HRID 536041 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([CH3:15])[CH3:14])=[C:8]([N+:16]([O-])=O)[CH:7]=1)(=[O:5])=[O:4]>C(O)C.[Pd]>[NH2:16][C:8]1[CH:7]=[C:6]([S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[CH:11]=[CH:10][C:9]=1[O:12][CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 1

HCID 699352384-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide

Product 1

HCID 434492953-amino-N-methyl-4-[(1-methylethyl)oxy]benzenesulfonamideYield 77.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of N-methyl-4-[(1-methylethyl)oxy]-3-nitrobenzenesulfonamide (1.6 g, 5.8 mmol) in ethanol (20 mL) under nitrogen, Pd/C (0.160 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 overnight at room temperature. The mixture was then filtered and concentrated to afford 3-amino-N-methyl-4-[(1-methylethyl)oxy]benzenesulfonamide (1.1 g, 77%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.01-7.10 (m, 2H), 6.87-6.98 (m, 2H), 5.08 (br. s., 2H), 4.63 (dt, J=5.93, 11.98 Hz, 1H), 2.34-2.41 (m, 3H), 1.29 (d, J=6.02 Hz, 6H); MS (m/z) 244.7 (M+H+)

Workup

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

Sources & evidence

ORD record
ord-aa418ae23a0d4180a0fcdf9abd261693
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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