Acetic Anhydride → 2,6-dimethyl-4H-3,1-benzoxazin-4-one

HRID 1197117Notes

Reaction equation

HRID 1197117 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=O)[CH3:13]>>[CH3:12][C:13]1[O:8][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 27965282,6-dimethyl-4H-3,1-benzoxazin-4-one

Procedure

45.5 g (0.3 mol) of 5-Methylanthranilic acid are refluxed together with 130 g of acetic anhydride for 3 hours. After the solvent has been evaporated in vacuo, the residue is dissolved in 200 ml of dichloromethane, and the solution is filtered through silica gel. The concentrated filtrate is induced to crystallise with isopropyl ether.

Workup

  1. customAfter the solvent has been evaporated in vacuo
  2. dissolutionthe residue is dissolved in 200 ml of dichloromethane
  3. filtrationthe solution is filtered through silica gel
  4. customto crystallise with isopropyl ether

Sources & evidence

ORD record
ord-870075bdc07e436cbec7a3fd48b81d16
Source dataset
uspto-grants-1992_05
Patent number
US05116971

Reaction notes

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