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

HRID 235581Notes

Reaction equation

HRID 235581 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-oneYield 74.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Iron powder (1.05 g) was suspended in 5% aqueous acetic acid (2.0 ml) and heated to 80° C. To the suspension, a solution of 7-fluoro-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.47 g) in acetic acid (1.9 ml) and ethyl acetate (1.9 ml) was dropwise added, and the resultant mixture was heated under reflux at 60° to 80° C. for 3 hours. After being allowed to cool, water and ethyl acetate were added to the mixture. The residue was removed by filtration, and the filtrate was extracted with ethyl acetate. The extract was washed with water and aqueous sodium bicarbonate solution, dried and concentrated to give 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.31 g). m.p., 183°-185° C.

Workup

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

Sources & evidence

ORD record
ord-21678158154448c08881820dcc10b381
Source dataset
uspto-grants-1987_02
Patent number
US04640707

Reaction notes

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