9-fluoro-7-nitro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine → 9-fluoro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazin-7-amine

HRID 56107Notes

Reaction equation

HRID 56107 reaction equation
[F:1][C:2]1[C:11]2[N:10]3[CH2:12][CH2:13][CH2:14][CH:9]3[CH2:8][O:7][C:6]=2[CH:5]=[C:4]([N+:15]([O-])=O)[CH:3]=1>C1COCC1.[Pd]>[F:1][C:2]1[C:11]2[N:10]3[CH2:12][CH2:13][CH2:14][CH:9]3[CH2:8][O:7][C:6]=2[CH:5]=[C:4]([NH2:15])[CH:3]=1

Participants

4

Reactant 1

HCID 853655159-fluoro-7-nitro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine

Product 1

HCID 731104369-fluoro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-fluoro-7-nitro-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine (4.00 g, 16.79 mmol) in THF (40 mL) was added Pd/C (1.50 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (3.00 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-1f7aa47fa83148df96975622d59acb56
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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