Ammonia → 2-Amino-3-fluorobenzamide

HRID 1687610Notes

Reaction equation

HRID 1687610 reaction equation
[F:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O1CCOCC1.C(=O)=O.[NH3:23]>>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH2:23])=[O:12]

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 280Carbon DioxideHCID 312751,4-DioxaneHCID 105353938-Fluoroisatoic anhydride

Product 1

HCID 152567912-Amino-3-fluorobenzamide

Procedure

A mixture of 8-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (2.00 g, 0.0110 mol) in 1,4-Dioxane (25 mL, 0.32 mol) was treated with ammonia (20 mL, 0.5 M in dioxane) and warmed to 60° C. for 2 h (dry ice cold finger). Additional ammonia (20 mL) was added and after 1 h at 60° C., solvent was evaporated to afford title compound.

Workup

  1. customsolvent was evaporated

Sources & evidence

ORD record
ord-1f663ea6978242509efa1f12b67a1a4a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…