6-Fluoro-9-nitro-2,3-dihydro-1H-benzo[b]azepine → 6-Fluoro-2,3,4,5-tetrahydro-1H-benzo[B]azepin-9-amine

HRID 243207Notes

Reaction equation

HRID 243207 reaction equation
[F:1][C:2]1[C:12]2[CH:11]=[CH: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[CH2:11][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 681578076-Fluoro-9-nitro-2,3-dihydro-1H-benzo[b]azepine

Product 1

HCID 681578656-Fluoro-2,3,4,5-tetrahydro-1H-benzo[B]azepin-9-amineYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-fluoro-9-nitro-2,3-dihydro-1H-benzo[b]azepine (225.4 mg, 1.0826 mmol) in EtOAc (15 mL) was added a slurry of 10% Pd/C (50 mg) in IMS (4 mL) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 20 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording the title compound as a purple oil (197 mg, quantitative). LCMS (Method J): RT 1.69 min [M+H]+ 181\

Workup

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

Sources & evidence

ORD record
ord-579dde28e50e401aba863fc704aa8c38
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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