4-methyl-8-nitro-2H-1,4-benzoxazin-3(4H)-one → 8-Amino-4-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 576074Notes

Reaction equation

HRID 576074 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-])=O)[C:6]=2[O:5][CH2:4][C:3]1=[O:15]>C(O)C.[Pd]>[NH2:12][C:11]1[C:6]2[O:5][CH2:4][C:3](=[O:15])[N:2]([CH3:1])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 389971764-methyl-8-nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 263703078-Amino-4-methyl-2H-1,4-benzoxazin-3(4H)-oneYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-methyl-8-nitro-2 H-1,4-benzoxazin-3(4 H)-one (415 mg, 1.99 mmol) in ethanol (10 mL) was added 10% palladium activated carbon (415 mg) at room temperature, and the mixture was stirred overnight under a hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark), followed by washing with ethanol. The filtrate was concentrated under reduced pressure. The resulting residue was dried under reduced pressure to afford the title compound as a gray powder (314 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite (registered trademark)
  2. washby washing with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was dried under reduced pressure

Sources & evidence

ORD record
ord-862f18eab74f4ad4bcf8f898dc1d921c
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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