Hydrochloric Acid → Ethyl 1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 1065110Notes

Reaction equation

HRID 1065110 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].[O-]CC.[Na+].[C:16](OCC)(=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18].[Na].Cl>C(O)C>[CH3:1][N:2]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:9](=[O:11])[CH:10]=[C:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 155795831-[2-(Methylamino)phenyl]ethan-1-one

Product 1

HCID 13223147Ethyl 1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

149 mgs (1 mMol) of 1-(2'-methylaminophenyl)ethanone was heated under reflux with 4 mMol of sodium ethoxide and 4 mMol of diethyl oxalate in 7 ml of ethanol for 11/2 hr. The reaction mixture, which contained the sodium salt of ethyl (2-N-methylaminobenzoyl)pyruvic acid was poured into dilute hydrochloric acid and extracted with chloroform. Evaporation to dryness and boiling the residue in diethyl ether afforded, after storing at 0°-5°, 160 mgs (70%) of the title product, mp 114°-5°.

Workup

  1. extractionextracted with chloroform
  2. customEvaporation to dryness
  3. customafforded
  4. customafter storing at 0°-5°

Sources & evidence

ORD record
ord-f03a62cbe82644da8f8f5ad122da8033
Source dataset
uspto-grants-1982_05
Patent number
US04328341

Reaction notes

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