Hydrochloric Acid → 2,8-Diethyl 6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate

HRID 1649029Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([OH:13])=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[NH2:17])(=[O:3])[CH3:2].[O-:18][CH2:19][CH3:20].[Na+].[C:22](OCC)(=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].[Na].Cl.[CH2:34]([OH:36])[CH3:35]>>[O:12]=[C:10]1[C:8]2[CH:9]=[C:4]3[C:5](=[C:6]([CH2:14][CH2:15][CH3:16])[C:7]=2[O:13][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:11]1)[NH:17][C:20]([C:19]([O:36][CH2:34][CH3:35])=[O:18])=[CH:2][C:1]3=[O:3]

Participants

Reactant 6

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 7268Diethyl Oxalate

HCID 2723922Sodium ethoxide

HCID 27752141-(5-acetyl-2-amino-4-hydroxy-3-propylphenyl)ethan-1-one

HCID 5360545Sodium

Product 1

HCID 132231582,8-Diethyl 6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylateYield 65%

Procedure

Treatment of the product of step (e) (1 mmole) with sodium ethoxide (10 mmole), in ethanol (10 ml) containing diethyl oxalate (10 mmole) at reflux for 3 hours, followed by acidification of the mixture, which contained the sodium salt of diethyl 4,4'-(2-amino-4-hydroxy-3-propylphenylene-1,3-diyl)bis(2,4-dioxo-butanoate), with gaseous HCl and heating under reflux for 1 hour afforded the subtitle compound which was isolated by dilution with water, extraction with chloroform, concentration and purification by column chromatography (yield 65%) mp 211°-212°.

Workup

temperatureat reflux for 3 hours
temperatureunder reflux for 1 hour

Sources & evidence

ORD record: ord-2021c1970620467d9cb9f56960fd2208
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04414416

Reaction notes

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