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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1900757Generated: October 29, 2026

Diethyl Ether → (+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

https://huagongshe.com/reaction/1900757

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantAcetic AnhydrideHCID 7918—
ReactantFormic anhydrideHCID 9548680—
Reactant2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneHCID 23369567—
SolventChloroformHCID 6212—
SolventTetrahydrofuranHCID 8028—
Product(+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneHCID 2336972937.9%

Reaction Conditions

Temperature70 °C

Reaction Steps

To a suspension of (-)-aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (965 mg, 4.19 mmol) in a mixture of tetrahydrofuran (30 ml) and chloroform (30 ml), acetic anhydride--formic anhydride (1.83 g, 20.8 mmol) was added and refluxed with heat in a bath of 70° C. for 3 hours. The temperature of the reaction mixture was returned to room temperature. Ether was added to the mixture and insoluble matter was collected by filtration. Recrystallization from chloroform--methanol--ether yielded 410 mg of the title compound as colorless powder (37.9%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05576324
Source datasetuspto-grants-1996_11
ORD IDord-c799883971d04d7c9aa90577fe37e9e8
Source noteuspto-grants-1996_11