Iodoethane → 4,4-Dimethyl-1-ethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarbonitrile

HRID 36399Notes

Reaction equation

HRID 36399 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12](O)=O)=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[C:4](=[O:17])[CH2:3]1.CC1(C)C2C(=CC(C(O)=O)=CC=2)[NH:23]C(=O)C1.CC1(C)C2C(=CC(C#N)=CC=2)NC(=O)C1.ICC.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:23])=[CH:9][CH:10]=2)[N:5]([CH2:15][CH3:16])[C:4](=[O:17])[CH2:3]1

Participants

7

Reactant 5

HCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 150777994,4-Dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acidHCID 150778004,4-Dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarbonitrileHCID 150778024,4-Dimethyl-1-ethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acid

Product 1

HCID 150778014,4-Dimethyl-1-ethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarbonitrileYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One prepared 4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acid analogously to the procedure for 4,4-dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarboxylic acid (DE-A-3,818,830) as follows: one stirred 4,4-dimethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarbonitrile (2.0 g, 10.0 mmol), iodoethane (1 ml, 12.0 mmol) and potassium carbonate (1.70 g, 12.0 mmol) for one hour at 60° C., again added iodoethane (2 ml, 24 mmol) and potassium carbonate (2.5 g, 25 mmol) thereto and stirred for one hour at 60° C. One allowed to cool to room temperature, stirred the solution into water, filtered off the precipitate with suction and dried in a vacuum. One obtains 4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-2-oxo-7-quinolinecarbonitrile (1.1 g, 48%) with the m.p.=120°-121° C.

Workup

  1. filtrationfiltered off the precipitate with suction
  2. customdried in a vacuum

Sources & evidence

ORD record
ord-0ff424f5b43a4079bc237d94d0b98811
Source dataset
uspto-grants-1995_05
Patent number
US05414088

Reaction notes

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