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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 328814Generated: October 30, 2026

Ethyl formate → 3-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

https://huagongshe.com/reaction/328814

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl formateHCID 8025—
ReactantSodium hydrideHCID 24758—
ReactantSodium ethoxideHCID 2723922—
ReactantBenzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylateHCID 15480673—
SolventBenzeneHCID 241—
SolventEthanolHCID 702—
Product3-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl esterHCID 86733855—

Reaction Steps

Following the procedure of Examples 1-E, 16-B and 17-B, 9.5 g. of benzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate, 10.95 ml. of ethyl formate and sodium ethoxide prepared from 2.57 g. of sodium hydride and 3.23 ml. of ethanol in 120 ml. of benzene gave on work-up a yellow oil which on crystallization afforded 6.0 g. of crude product, m.p. 106°-110° C. The analytical same is recrystallized several times from methanol, m.p. 116°-118° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04018758
Source datasetuspto-grants-1977_04
ORD IDord-db58b3f5061145f28d6f1870dd77da35
Source noteuspto-grants-1977_04