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Diethyl Oxalate → Ethyl 4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 1649025
Notes
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Reaction equation

HRID 1649025 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[O-]CC.[Na+].[C:15](OCC)(=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Na].C(C(C(=O)C1C=CC=CC=1N)C(=O)C(O)=O)C>C(O)C>[O:10]=[C:8]1[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7268Diethyl OxalateHCID 110862'-AminoacetophenoneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 53727144HCID 53727144, compound

Product 1

HCID 282844Ethyl 4-oxo-1,4-dihydroquinoline-2-carboxylateYield 58%

Reagents, catalysts & solvents

1
HCID 702EthanolSolvent

Procedure

1.35 g (10 mMol) of 1-(2'-aminophenyl)ethanone was heated under reflux with 40 mMol of sodium ethoxide and 40 mMol of diethyl oxalate in 70 ml of ethanol for 21/2 hr. The reaction mixture, which contained the sodium salt of ethyl (2-aminobenzoyl)pyruvic acid was poured into ice/hydrochloric acid and extracted with chloroform. Concentration to dryness and boiling with diethyl ether gave 1.25 g (58%) of the title product, mp 210°-212°.

Workup

  1. extractionextracted with chloroform
  2. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-f181898075924034853ec6010df1eac2
Source dataset
uspto-grants-1983_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04414416

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes