4-Fluoro-1-nitro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocycloheptene → 4-Fluoro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten-1-ylamine

HRID 243228Notes

Reaction equation

HRID 243228 reaction equation
[F:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[C:5]([NH2:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 681580754-Fluoro-1-nitro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocycloheptene

Product 1

HCID 681578084-Fluoro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten-1-ylamineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-1-nitro-6,7,8,9-tetrahydro-5-oxa-9-azabenzocycloheptene (158 mg, 0.746 mmol) in EtOAc (10 mL) was added a slurry of 10% Pd/C (30 mg) in IMS (1 mL) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 18 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording the title compound as a brown solid (131.5 mg, 97%). 1H NMR (CDCl3, 300 MHz): 6.46 (1H, dd, J=10.2, 8.6 Hz), 6.35 (1H, dd, J=8.7, 5.1 Hz), 4.25 (2H, t, J=5.8 Hz), 3.36-3.32 (5H, bs & m), 2.06 (2H, quintet, J=5.8 Hz)

Workup

  1. filtrationThe suspension was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-13892f4e98834ae4a58fef822da35d5e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…