7-Fluoro-2-methylisatoicanhydride → Methyl 4-fluoro-2-(methylamino)benzoate

HRID 542797Notes

Reaction equation

HRID 542797 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[O:7][C:8](=O)[N:9]([CH3:10])[C:4]=2[CH:3]=1.C[O-].[Na+]>CO>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:7][CH3:8])=[O:12])=[C:4]([NH:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 103302747-Fluoro-2-methylisatoicanhydrideHCID 10942334Sodium Methoxide

Product 1

HCID 13474393Methyl 4-fluoro-2-(methylamino)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 7-fluoro-1-methyl-1H-3,1-benzoxazine-2,4-dione (20.0 g) and methanol (103 ml) was boiled under reflux. To the boiling mixture was added dropwise a solution of sodium methoxide (0.06 g) in methanol (50 ml.) during 19 minutes. The mixture was distilled in vacuo to remove solvent and give the product as a residue. There was thus obtained the novel compound methyl 4-fluoro-2-methylaminobenzoate as an oil which solidified on standing and was suitable for use in the next stage of synthesis. An analytical sample was prepared by distillation in vacuo followed by recrystallisation of the distillate from aqueous isopropanol. This sample had m.p. 39°-39.5°.

Workup

  1. temperatureunder reflux
  2. distillationThe mixture was distilled in vacuo
  3. customto remove solvent
  4. customgive the product as a residue

Sources & evidence

ORD record
ord-f6a1bfbb73bb45619b016cb4f2ea1922
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

Loading…