N-(indan-5-yl)-5-nitro-2-thiophen-2-yl-benzamide → 5-amino-N-(indan-5-yl)-2-(thiophen-2-yl)-benzamide

HRID 1531278Notes

Reaction equation

HRID 1531278 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:26])[C:12]3[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=3[C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[NH2:18][C:16]1[CH:15]=[CH:14][C:13]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[C:12]([CH:17]=1)[C:11]([NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2)=[O:26]

Participants

4

Reactant 1

HCID 21253368N-(indan-5-yl)-5-nitro-2-thiophen-2-yl-benzamide2×

Product 1

HCID 212533725-amino-N-(indan-5-yl)-2-(thiophen-2-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound of Example 5, N-(indan-5-yl)-5-nitro-2-thiophen-2-yl-benzamide (0.083 g, 0.228 mmol) in ethyl acetate (10 mL) is degassed and 10% palladium on carbon added. The reaction mixture is evacuated and placed under 1 atm H2(g) for 16 h. Filtration of the reaction mixture through Celite is followed by concentration of the filtrate under reduced pressure to give 5-amino-N-(indan-5-yl)-2-(thiophen-2-yl)-benzamide as an oil which foams to a solid on treatment with diethyl ether. mp 62-67° C. MS (ES+), m/z 335 (M+1).

Workup

  1. customThe reaction mixture is evacuated
  2. filtrationFiltration of the reaction mixture through Celite

Sources & evidence

ORD record
ord-ed11454e6d654e559277da24938dd3fb
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

Loading…