6-nitro-3,4-dihydro-2H-1,4-benzoxazine → 3,4-Dihydro-2H-1,4-benzoxazin-6-amine

HRID 25146Notes

Reaction equation

HRID 25146 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:13]=1)([O-])=O>CO.[Pd]>[O:12]1[C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:13][C:8]=2[NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 113441023,4-Dihydro-2H-1,4-benzoxazin-6-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine (1.8 g, 10.0 mmol) in methanol (150 mL) was hydrogenated on a Parr hydrogenator for 6 hours with 10% palladium on carbon (1.06 g) as a catalyst. The reaction mixture was filtered through Celite to remove the catalyst and the Celite rinsed with methanol. The filtrate was evaporated under vacuum to yield 3,4-dihydro-2H-benzo[1,4]oxazin-6-yl amine as a solid product.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove the catalyst
  3. washthe Celite rinsed with methanol
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-d811f28b55294d70b508b3aedf4b2ef0
Source dataset
uspto-grants-2005_02
Patent number
US06858621B2

Reaction notes

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