Acetic Anhydride → 8-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one

HRID 459891Notes

Reaction equation

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 184442558-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one

Procedure

A solution of 2-amino-3-chlorobenzoic acid (4.93 g, 28.7 mmol) in acetic anhydride (15 mL) was refluxed for 3 h, then cooled to room temperature. The precipitated solid was filtered, and washed with hexane. The title compound was obtained as a brown solid (4.33 g). 1H NMR (500 MHz, CDCl3) δ 8.11 (d, J=8 Hz, 1H), 7.86 (d, J=8 Hz, 1H), 7.43 (t, J=8 Hz, 1H), 2.54 (s, 3H).

Workup

filtrationThe precipitated solid was filtered
washwashed with hexane

Sources & evidence

ORD record: ord-f7dc9876ec4f4610936e53a24463a7b7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196079B2

Reaction notes

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