HCID 2058492, compound → 2-amino-N-cyclopentylbenzenesulfonamide

HRID 1487232Notes

Reaction equation

HRID 1487232 reaction equation
[CH:1]1([NH:6][S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:9])=[O:8]

Participants

4

Reactant 1

HCID 2058492HCID 2058492, compound

Product 1

HCID 11328322-amino-N-cyclopentylbenzenesulfonamideYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-cyclopentyl-2-nitrobenzenesulfonamide (23 g, 85.2 mmol) in methanol (500 mL) was added palladium on carbon (10%). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated to afford the product 2-amino-N-cyclopentylbenzenesulfonamide (20 g, yield 97.8%). 1H NMR (400 MHz, CDCl3) δ ppm 7.71-7.74 (dd, 1H, J=1.2 Hz, 8.0 Hz), 7.30-7.34 (m, 1H), 6.75-6.82 (m, 2H), 4.86 (br s, 3H), 3.50-3.53 (m, 1H), 1.67-1.69 (m, 2H), 1.55-1.62 (m, 2H), 1.42-1.50 (m, 2H), 1.22-1.36 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-510b09d328b9465a9627ee540b674940
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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