Ethyl orthoformate → 5,7-Dimethoxy-4H-benzo[d][1,3]oxazin-4-one

HRID 130325Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[C:10]([O:12][CH3:13])[CH:11]=1)[C:7]([OH:9])=[O:8].[CH2:15](OC(OCC)OCC)C>>[CH3:13][O:12][C:10]1[C:6]2[C:7](=[O:9])[O:8][CH:15]=[N:14][C:5]=2[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 116584562-Amino-4,6-dimethoxybenzoic acid

Product 1

HCID 115358035,7-Dimethoxy-4H-benzo[d][1,3]oxazin-4-oneYield 76.2%

Conditions

Temperature: 140 °C

Procedure

A mixture of 1.0 g (5.07 mmol) of 4,6-dimethoxy-anthranilic acid, as prepared in Example 3, and 15 ml of triethylorthoformate (90.2 mmol) was heated to 140° C. for 4 h. The volatiles were evaporated under reduced pressure to give 0.8 g of 5,7-dimethoxy-3,1-benzoxazine-4-one as a yellow solid (76% yield), which was used without any further purification.

Workup

customThe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record: ord-ac62deacc0d741cb94b3a4f38d537f2c
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381730B2

Reaction notes

Loading…