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

HRID 243235Notes

Reaction equation

HRID 243235 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@@H:8]([CH3:12])[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:11]2[O:10][CH2:9][C@@H:8]([CH3:12])[NH:7][C:6]=2[C:5]([NH2:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68157836(R)-8-Fluoro-3-methyl-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 68158450(R)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamineYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (R)-8-fluoro-3-methyl-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine (183 mg, 0.86 mmol) and 10% Pd/C (37 mg) in EtOAc (12 mL) and IMS (1.2 mL) was stirred under a H2 balloon for 16 h. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to give the title compound as a pale yellow oil (162 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 6.36 (1H, dd, J=10.6, 8.6 Hz), 6.14 (1H, dd, J=8.6, 4.6 Hz), 4.19 (1H, dd, J=10.4, 2.7 Hz), 3.65 (1H, dd, J=10.4, 8.0 Hz), 3.44 (1H, dqd, J=8.0, 6.5, 2.7 Hz), 3.13 (3H, br s), 1.17 (3H, d, J=6.5 Hz)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c555ed462a75415f97aab36c0e48f0bd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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