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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence