Acetic Anhydride → 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one

HRID 1777248Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14](OC(=O)C)(=O)[CH3:15]>>[CH3:14][C:15]1[O:5][C:4](=[O:6])[C:3]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 957952-Amino-6-nitro-benzoic acid

Product 1

HCID 666429832-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one

Procedure

In certain embodiments, step (a) (i.e., reacting 2-amino-6-nitrobenzoic acid with acetic anhydride in a solvent to form 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one) is conducted at a temperature ranging from about 50 to about 150° C., from about 75 to about 120° C., from about 75 to about 100° C., from about 80 to about 100° C., from about 80 to about 95° C., or from about 85 to about 90° C. In certain embodiments, step (a) is conducted at a temperature from about 85 to about 90° C.

Sources & evidence

ORD record: ord-ecb94304f50547c8ad4e8b1752aaf27e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266858B2

Reaction notes

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