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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 481022Generated: October 25, 2026

Ethyl orthoformate → 7-Chloro-3H-quinazolin-4-one

https://huagongshe.com/reaction/481022

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl orthoformateHCID 31214—
Reactant1,4-DioxaneHCID 31275—
ReactantSodium BicarbonateHCID 516892—
Reactant2-Amino-4-chlorobenzamideHCID 12374837—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product7-Chloro-3H-quinazolin-4-oneHCID 135416175—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a solution of 2-amino-4-chlorobenzamide (58 g, 0.34 mol) in hot (60° C.) N-methylpyrrolidone (170 mL), triethylorthoformate (151 g, 1.02 mol, 3 equiv) and a 1,4-dioxane 5N HCl solution (ca. 15 mL) were added. The resulting solution was heated at 110° C. for 18 h. Then, the mixture was cooled to room temperature, was poured over cold water and was brought to pH 7 with saturated NaHCO3 solution. The formed precipitate was filtered, washed with water and dried to give the desired product as a slightly beige solid (58 g, 94%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06653475B2
Source datasetuspto-grants-2003_11
ORD IDord-ff4645a754444b7eb3b86fe3ed7b1d6e
Source noteuspto-grants-2003_11