8-Fluoro-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine → 8-Fluoro-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine

HRID 243221Notes

Reaction equation

HRID 243221 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[C:5]([N+:12]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[C:5]([NH2:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 681576788-Fluoro-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 681576428-Fluoro-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-fluoro-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine (290 mg, 1.463 mmol) in EtOAc (15 mL) was added a slurry of 10% Pd/C (50 mg) in IMS (2 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 purple oil (243 mg, 99%).

Workup

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

Sources & evidence

ORD record
ord-b29081e98ea44aeca0338f78a348b3c4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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