N-[5-(3-nitrophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide → N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 18420Notes

Reaction equation

HRID 18420 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH2:13]3)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH2:13]3)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 46900137N-[5-(3-nitrophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

Product 1

HCID 46899970N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Intermediate 3 (430 mg, 1.19 mmol) in ethanol (10 ml) was treated with 10% palladium on charcoal (paste) (100 mg), and then stirred under an atmosphere of hydrogen at room temperature and pressure for 24 h. The mixture was filtered through a bed of kieselguhr and washed through with ethanol. The filtrate was removed under reduced pressure to give the title compound as a colourless solid (320 mg, 81%); mass spectrum: (ES−): Found 329 (MH−); C18H22N2O2S requires 330; 1H-NMR (400 MHz, CDCl3) δ 1.36 (6H, m), 2.94 (2H, m), 3.17 (1H, m), 3.35 (2H, m), 3.77 (2H, bs), 4.31 (2H, m), 6.67 (1H, m), 6.87 (1H, m), 6.95 (1H, m), 7.22 (2H, m), 7.39 (2H, m).

Workup

  1. filtrationThe mixture was filtered through a bed of kieselguhr
  2. washwashed through with ethanol
  3. customThe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-08ecd2b2093a410da811f0b925670615
Source dataset
uspto-grants-2010_06
Patent number
US07741351B2

Reaction notes

Loading…