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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1283823Generated: November 2, 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/1283823

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 6-8, 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 numberUS03976650
Source datasetuspto-grants-1976_08
ORD IDord-84c0d92cd17d4c2d9286263c800b60e5
Source noteuspto-grants-1976_08