Iodoethane → Ethyl 1-ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

HRID 444200Notes

Reaction equation

HRID 444200 reaction equation
[OH:1][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].[CH2:24](I)[CH3:25]>CN(C)C=O>[CH2:24]([N:5]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[C:11]=2[C:2](=[O:1])[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4]1)[CH3:25]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 178469478HCID 178469478, compound

Product 1

HCID 12876363Ethyl 1-ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

By the method described in Japanese Patent Application No. 24956/1978, diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate was prepared from 3-amino-2-cyclohexenone and diethyl ethoxymethylenemalonate. The product was cyclized under heat to form ethyl 4-hydroxy-5-oxo-5,6,7,8-tetrahydroquinonine-3-carboxylate, followed by hydrolysis. The resulting ethyl 4-hydroxy-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate (2.35 g) was suspended in 80 ml of dimethylformamide. The suspension was heated to 60° C., and 1.52 g of potassium carbonate and 1.54 g of ethyl iodide were added, and the mixture was stirred at 70° C. for 30 minutes. Further, 3.46 g of ethyl iodide was added, and the mixture was stirred for 1 hour. The insoluble matter was removed by filtration, and the mother liquor was concentrated to dryness. The product was extracted with chloroform, and the chloroform was distilled off. Methylene chloride was added to the residue, and the insoluble matter was collected by filtration. There was obtained 2.4 g of the captioned product as a light yellow powder. The nuclear magnetic resonance spectrum (DMSO-d6, 60 MC, TMS) had signals at δ1.2-1.5 (6H, m), 1.8-3.3 (6H, m), 4.0-4.5 (4H, m), and 8.4 (1H, s).

Workup

  1. customfollowed by hydrolysis
  2. stirringthe mixture was stirred for 1 hour
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe mother liquor was concentrated to dryness
  5. extractionThe product was extracted with chloroform
  6. distillationthe chloroform was distilled off
  7. additionMethylene chloride was added to the residue
  8. filtrationthe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-65eb62cd8a684ab7ad4fb067edf0b42d
Source dataset
uspto-grants-1981_04
Patent number
US04263302

Reaction notes

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