Water → 6-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1030962Notes

Reaction equation

HRID 1030962 reaction equation
[F:1][C:2]1[C:15]([N+:16]([O-])=O)=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.O>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:16][C:15]1[C:2]([F:1])=[CH:3][C:4]2[O:9][CH2:8][C:7](=[O:10])[N:6]([CH2:11][C:12]#[CH:13])[C:5]=2[CH:14]=1

Participants

6

Reactant 2

HCID 962WaterHCID 137312997-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 111603236-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

Iron powder (1.05 g) is suspended in 5% aqueous acetic acid (2.0 ml) and heated to 80° C. To the suspension, a solution of 7-fluoro-3,4-dihydro-3-oxo-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazine (0.47 g) in acetic acid (1.9 ml) and ethyl acetate (1.9 ml) is dropwise added, and the resulting mixture is heated under reflux at 60° to 80° C. for 3 hours. After being allowed to cool, water and ethyl acetate are added to the mixture. The residue is removed by filtration, and the filtrate is extracted with ethyl acetate. The extract is washed with water and aqueous sodium bicarbonate solution, dried and concentrated to give 6-amino-7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux at 60° to 80° C. for 3 hours
  3. temperatureto cool
  4. customThe residue is removed by filtration
  5. extractionthe filtrate is extracted with ethyl acetate
  6. washThe extract is washed with water and aqueous sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d3f237b11c5845eb81e2e2c32b17ddd8
Source dataset
uspto-grants-1992_04
Patent number
US05108488

Reaction notes

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