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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 215794Generated: October 26, 2026

Methanol → 2-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dione

https://huagongshe.com/reaction/215794

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantSodium hydrideHCID 24758—
Reactant5-Chloroisatoic anhydrideHCID 78480—
Reactant5-FluoroisatinHCID 236566—
SolventChloroformHCID 6212—
SolventDimethylformamideHCID 6228—
Product2-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dioneHCID 478569—

Reaction Steps

To a suspension of NaH (10 mmol, 40 mg 60%) in 4 mL of DMF was added 10 mmol of 5-fluoroisatin in 2 mL of DMF. After 15 min, a solution of 5-chloroisatoic anhydride in 3 mL of DMF was added. The reaction mixture was stirred for 18 h, methanol (0.5 mL) and 20 mL of chloroform was added and the organic solution was washed with water, dried (MgSO4) and concentrated to give a residue that was purified by silica gel chromatography (CHCl3:CH3OH). Yield 77%: mp 280-282° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08193185B2
Source datasetuspto-grants-2012_06
ORD IDord-fd13265b4c7b46ac9ab24a8ebf6c8904
Source noteuspto-grants-2012_06