4-Methyl-6-nitro-2H-1,4-benzoxazin-3-one → 6-amino-4-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 386661Notes

Reaction equation

HRID 386661 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:15]>CCO.O.[Fe]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]2[O:5][CH2:4][C:3](=[O:15])[N:2]([CH3:1])[C:7]=2[CH:8]=1

Participants

5

Reactant 1

HCID 14777644-Methyl-6-nitro-2H-1,4-benzoxazin-3-one

Product 1

HCID 27644636-amino-4-methyl-2H-1,4-benzoxazin-3(4H)-oneYield 97.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Fe powder (4.1 g, 73.20 mmol) was added to a solution of 4-methyl-6-nitro-4H-benzo[1,4]oxazin-3-one (3.0 g, 14.42 mmol) in EtOH (100 ml) and water (50 ml). The mixture was stirred at 60° C. vigorously with a mechanic stirrer for 18 hours, then filtered through a celite cake. The filtrate was concentrated under reduced pressure to give 2.50 g of 6-amino-4-methyl-4H-benzo[1,4]oxazin-3-one as a solid, 98%.

Workup

  1. filtrationfiltered through a celite cake
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74d5da20edcb49839e92a81f092250e0
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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