2-Methoxy-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)-2-methoxy-ethanone

HRID 1041703Notes

Reaction equation

HRID 1041703 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)=[O:5]>[Pd].C(O)C>[NH2:17][C:15]1[CH:14]=[CH:13][C:12]2[N:6]([C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH2:7][CH2:8][CH2:9][O:10][C:11]=2[CH:16]=1

Participants

4

Reactant 1

HCID 672634692-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

Product 1

HCID 672643221-(3-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-methoxy-ethanoneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methoxy-1-(3-nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone (269 mg, 1.01 mmol) and 10% Palladium on Carbon (50% Wet) (65 mg) in Ethanol (10 mL) was shaken under an atmosphere of Hydrogen (40 psi) for 6 h. Following filtration and conc., 1-(3-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-methoxy-ethanone (202 mg, 85%) was isolated as white solids. 1H-NMR (CDCl3): 7.05 (d, 1H, J=8.2 Hz), 6.80 (m, 2H), 4.79 (m, 1H), 4.40 (m, 1H), 4.02 (m, 1H), 3.72 (m, 1H), 3.60 (m, 1H), 3.34 (s, 3H), 2.72 (m, 1H), 2.24 (m, 1H), 1.78 (m, 1H).

Workup

  1. filtrationfiltration

Sources & evidence

ORD record
ord-faef5097559b484f8139b788de5a53d7
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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