HCID 67263601, compound → 1-(2-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone

HRID 1041675Notes

Reaction equation

HRID 1041675 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][N:9]([C:14](=[O:16])[CH3:15])[C:8]=2[CH:17]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][N:9]([C:14](=[O:16])[CH3:15])[C:8]=2[CH:17]=1

Participants

4

Reactant 1

HCID 67263601HCID 67263601, compound

Product 1

HCID 672643681-(2-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanoneYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone (0.520 g, 2.20 mmol) and 10% Palladium on Carbon (50% Wet) (0.12 g) in Ethanol (40 mL) was shaken under an atmosphere of Hydrogen (30 psi) overnight. The mixture was filtered and washed with ethanol (100 mL). Conc. in vacuo afforded 1-(2-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-ethanone (450 mg, 99%). 1H-NMR (CDCl3): 6.94 (d, 1H, J=8.1 Hz), 6.32 (d, 1H, J=8.1 Hz), 6.56 (s, 1H), 4.78 (m, 1H), 4.36 (m, 1H), 3.58 (m, 1H), 2.69 (m, 1H), 2.22 (m, 1H), 1.93 (s, 3H), 1.73 (m, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ethanol (100 mL)

Sources & evidence

ORD record
ord-74a35bdb5b0d4dfea8564e6dd9fcf461
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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