Acetic Anhydride → 8-iodo-2,7-dimethyl-4H-benzo[d][1,3]oxazin-4-one

HRID 2092297Notes

Reaction equation

HRID 2092297 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](OC(=O)C)(=O)[CH3:14]>>[I:11][C:10]1[C:2]2[N:1]=[C:13]([CH3:14])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=[CH:8][C:9]=1[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 457896112-Amino-3-iodo-4-methylbenzoic acid

Product 1

HCID 584664568-iodo-2,7-dimethyl-4H-benzo[d][1,3]oxazin-4-oneYield 82%

Procedure

2-Amino-3-iodo-4-methylbenzoic acid (10 g, 36 mmol) was treated with acetic anhydride (70 mL) and the mixture stirred at reflux for 4 h. The reaction was allowed to cool down to RT and placed in an ice bath for ˜2 h. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to give 8-iodo-2,7-dimethyl-4H-benzo[d][1,3]oxazin-4-one (8.9 g, 82%) as a tan solid. MS (M+H)+ 302.

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-7983dd98af5c48e38a02d91d7887d9a5
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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