Sodium hydride → 5-Choro-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrile

HRID 598177Notes

Reaction equation

HRID 598177 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18](Cl)[C:3]=1[C:4](/[C:6](=[CH:9]/[NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])/[C:7]#[N:8])=[O:5].[H-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:3]=1[C:4](=[O:5])[C:6]([C:7]#[N:8])=[CH:9][N:10]2[CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67267339(E)-2-(2,6-dichlorobenzoyl)-3-(1-propylbutylamino)acrylonitrile

Product 1

HCID 672675855-Choro-4-oxo-1-(1-propylbutyl)-1,4-dihydroquinoline-3-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(E)-2-(2,6-dichlorobenzoyl)-3-(1-propylbutylamino)acrylonitrile (0.020 g, 0.059 mmol) was dissolved in dioxane (2 mL). Sodium hydride (0.007 g, 0.18 mmol, 60% wt. dispersion in mineral oil) was added in one portion. Reaction was heated overnight at 100° C. Solution was cooled and quenched with MeOH and concentrated. Flash chromatography gave the desired product (0.007 g, 40%)

Workup

  1. customReaction
  2. temperatureSolution was cooled
  3. customquenched with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a30f4e99ae47443fb4fb4f827b962785
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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