Acetyl chloride → HCID 12895018, compound

HRID 2371437Notes

Reaction equation

HRID 2371437 reaction equation
[C:1](Cl)(=O)[CH3:2].[F:5][C:6]1[CH:7]=[C:8]([NH2:15])[C:9](=[CH:13][CH:14]=1)[C:10]([OH:12])=[O:11]>C(OC(=O)C)(=O)C>[F:5][C:6]1[CH:14]=[CH:13][C:9]2[C:10](=[O:12])[O:11][C:1]([CH3:2])=[N:15][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 12895018HCID 12895018, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of acetyl chloride (4.6 ml) and 4-fluoroanthranilic acid (5 g) in acetic anhydride (100 ml) was heated under reflux for 48 hours, cooled and filtered. The filtrate was added to ice/water, stirred for 1 hour and extracted with ethyl acetate. The extract was dried and the solvent removed under reduced pressure to give 7-fluoro-2-methyl-3,1-benzoxazin-4-one, m.p. 159°-160°. (Compound 2).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. additionThe filtrate was added to ice/water
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1c542855d0c34a9c9d677f5839397ba9
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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