Acetic Anhydride → HCID 18317813, compound

HRID 1700118Notes

Reaction equation

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 2702592-Amino-3-bromobenzoic acid

Product 1

HCID 18317813HCID 18317813, compoundYield 80%

Conditions

Temperature: 110 °C

Procedure

Part A: A mixture of 19.2 g (89 mmol) of 2-amino-3-bromo benzoic acid (Beistein vol 14,369,vol IV,pg 1080) and 75 ml (0.79 mol) of acetic acid anhydride was heated to 110° C. under nitrogen with stirring for 3 hours. After cooling the mixture was concentrated in vacuo and co-evaporated twice with toluene. The product was purified over silicagel using CH2Cl2 as the eluent. A total of 17.0 g of 2-methyl-8-bromo-3,1-benzoxazin-4-one was obtained (80% yield).

Workup

temperatureAfter cooling the mixture
concentrationwas concentrated in vacuo
customThe product was purified over silicagel

Sources & evidence

ORD record: ord-b476f1d00b164ff692dbb7303dba0ba6
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350750B1

Reaction notes

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