N-Cyclobutyl-2-nitrobenzene-1-sulfonamide → HCID 62414720, compound

HRID 1487230Notes

Reaction equation

HRID 1487230 reaction equation
[CH:1]1([NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:6]([NH:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)(=[O:8])=[O:7]

Participants

4

Reactant 1

HCID 68284532N-Cyclobutyl-2-nitrobenzene-1-sulfonamide

Product 1

HCID 62414720HCID 62414720, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-cyclobutyl-2-nitrobenzenesulfonamide (7 g, 27.3 mmol) in methanol (100 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-cyclobutylbenzenesulfonamide (6 g, yield 97.1%). 1H NMR (400 MHz, CDCl3) δ ppm 7.68-7.71 (dd, 1H, J=1.6 Hz, 8.0 Hz), 7.27-7.33 (m, 1H), 6.74-6.82 (m, 2H), 5.30 (s, 1H), 5.08 (s, 2H), 3.70-3.73 (m, 1H), 1.96-2.04 (m, 2H), 1.67-1.75 (m, 2H), 1.48-1.62 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-66df88e6014c4895b8b4e97c121b97b1
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

Loading…