1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone → 1-(3-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1688041Notes

Reaction equation

HRID 1688041 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[N:8]([C:13](=[O:15])[CH3:14])[CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]2[N:8]([C:13](=[O:15])[CH3:14])[CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 672644451-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

Product 1

HCID 672635641-(3-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanoneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone (0.225 g, 0.952 mmol) was shaken with 10% Palladium on Carbon (50% Wet) (51 mg) in Ethanol (10 mL) under an atmosphere of Hydrogen (40 psi) for 6 h. Filtration and conc. afforded 1-(3-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone as white solids (195 mg, 99%). 1H-NMR (CDCl3): 7.06 (d, 1H, J=8.2 Hz), 6.81 (m, 2H), 4.78 (m, 1H), 4.40 (m, 1H), 2.72 (m, 1H), 2.23 (m, 1H), 1.89 (s, 3H), 1.81 (m, 2H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-14dfb399e8d641528531d9f17e2befde
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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