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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1255969Generated: November 3, 2026

Formamide → 4-Chloro-7-fluoro-6-nitroquinazoline

https://huagongshe.com/reaction/1255969

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormamideHCID 713—
ReactantNitric AcidHCID 944—
ReactantSulfuric AcidHCID 1118—
ReactantThionyl ChlorideHCID 24386—
Reactant4-Fluoroanthranilic acidHCID 2724967—
ReactantHCID 178518022HCID 178518022—
ReactantHCID 178526403HCID 178526403—
SolventDimethylformamideHCID 6228—
Product4-Chloro-7-fluoro-6-nitroquinazolineHCID 10609358—
ProductHCID 87756995HCID 87756995—

Reaction Steps

4-Chloro-7-fluor-6-nitroquinazoline was prepared as described in Mishani et al. (2005). In brief, 2-amino-4-fluorobezoic acid was reacted with formamide, at 160° C. for 3 hours. The resulting 7-fluoro-4-hydroxyquinazoline (Compound 22) was then reacted with a mixture of nitric acid and sulfuric acid, at 100° C., for 2 hours, to thereby obtain 7-fluoro-4-hydroxy-6-nitroquinazoline (Compound 23), which was thereafter reacted with thionyl chloride in DMF (reflux, 7 hours), to obtain 4-chloro-fluoro-6-nitroquinazoline (Compound 24, see, FIG. 3).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08461166B2
Source datasetuspto-grants-2013_06
ORD IDord-6f2573759f40405990c81c5ffd7ef37e
Source noteuspto-grants-2013_06