Pyridine → HCID 69671260, compound

HRID 529875Notes

Reaction equation

HRID 529875 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:12][CH:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])=[CH:9][C:10]#[N:11].[CH:18]1([CH2:21][C:22](Cl)=[O:23])C[CH2:19]1.N1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:12][CH:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])=[C:9]([C:22](=[O:23])[CH2:21][CH2:18][CH3:19])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 143262682-Cyclopropylacetyl chlorideHCID 69671093HCID 69671093, compound

Product 1

HCID 69671260HCID 69671260, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(2-chlorophenyl)-3-[(3-methylbutan-2-yl)amino]acrylonitrile (1 g, 4.02 mmol, 1 eq.) in 1,2-dichloroethane (2 ml) were added cyclopropylacetyl chloride (1.71 g, 16.08 mmol, 4 eq.) and pyridine (1.58 g, 20.1 mmol, Seq.) and the solution was heated to 80° C. for 8 h. The reaction was quenched with 1N aq. HCl (20 ml) and extracted with ethylacetate. The organic layers were combined and washed with 1N aq. NaOH (20 ml), dired over MgSO4 and concentration under vacuum. The residual oil was subjected to column chromatography to give 2-{(2-chlorophenyl)[(3-methylbutan-2-yl)amino]methylene}-3-oxohexanenitrile (1.012 g, 75% yield).

Workup

  1. customThe reaction was quenched with 1N aq. HCl (20 ml)
  2. extractionextracted with ethylacetate
  3. washwashed with 1N aq. NaOH (20 ml), dired over MgSO4 and concentration under vacuum

Sources & evidence

ORD record
ord-571ec33ce857474d9dc383940599cbad
Source dataset
uspto-grants-2016_05
Patent number
US09351489B2

Reaction notes

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