Acetic Anhydride → 7-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one

HRID 2209280Notes

Reaction equation

HRID 2209280 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=O)[CH3:13]>>[Br:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[O:5][C:12]([CH3:13])=[N:1][C:2]=2[CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 886912-Amino-4-bromobenzoic acid

Product 1

HCID 126761197-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-oneYield 49.2%

Conditions

Temperature
130 °C

Procedure

2-amino-4-bromobenzoic acid (825 mg, 3.82 mmol) was taken up in acetic anhydride (5.2 mL, 55.01 mmol) and mixture was heated at 130° C. After 4 hours, reaction mixture was cooled to rt and left there for two hours. The solid that precipitated was filtered and washed with cold ether, and dried in-vacuo to yield 7-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one 7.25 (451 mg), which was used in the next step without further purification.

Workup

  1. customreaction mixture
  2. temperaturewas cooled to rt
  3. waitleft there for two hours
  4. customThe solid that precipitated
  5. filtrationwas filtered
  6. washwashed with cold ether
  7. customdried in-vacuo

Sources & evidence

ORD record
ord-71b3258ce6e64bf2b3aa58cbffe46d94
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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