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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1970051Generated: November 2, 2026

Acetic Acid → 8-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

https://huagongshe.com/reaction/1970051

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantFormaldehydeHCID 712—
ReactantMorpholineHCID 8083—
Reactant8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateHCID 86627550—
CatalystCopper iodideHCID 83717—
Solvent1,4-DioxaneHCID 31275—
Product8-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateHCID 8662755712.4%

Reaction Conditions

Temperature85 °C

Reaction Steps

15 mg (0.17 mmol) of para-formaldehyde, 15 mg (0.17 mmol) of morpholine and 3 mg (0.02 mmol) of copper iodide are added to a suspension of 47 mg (0.17 mmol) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 5 ml of anhydrous dioxan, then a drop of acetic acid is added and the mixture is heated at 85° C. for 48 hours. The raw reaction product is then filtered, the filtrate is evaporated and the residue is purified by preparative LCMS to give 4 mg (6%) of 8-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08426437B2
Source datasetuspto-grants-2013_04
ORD IDord-8238585474ac455e8dddcc24e92d73f8
Source noteuspto-grants-2013_04