2-Chlorobenzaldehyde → HCID 178439374, compound

HRID 489370Notes

Reaction equation

HRID 489370 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][C:11]1[CH:15]=[CH:14][NH:13][N:12]=1.[C:16]([CH2:18][C:19](=O)[CH2:20][CH2:21][CH3:22])#[N:17]>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:18]([C:16]#[N:17])=[C:19]([CH2:20][CH2:21][CH3:22])[NH:10][C:11]2=[N:12][NH:13][CH:14]=[C:15]12

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 97937233-OxohexanenitrileHCID 178418806HCID 178418806, compound

Product 1

HCID 178439374HCID 178439374, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of acetonitrile (4.8 g) in THF (150 mL) was added n-BuLi (67 mmol) at −78° C. Further, methyl butanoate (10 g) was added and the mixture was stirred for one hour. After acidification with hydrochloric acid, the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (10:1)) to give 1-cyanopentan-2-one (5.5 g) as a colorless oil. A solution of 2-chlorobenzaldehyde (1.9 g), 3-aminopyrazole (1.0 g) and 1-cyanopentan-2-one (1.6 g) in acetonitrile (20 mL) was heated under reflux overnight. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration to give the title compound (1.3 g) as colorless crystals.

Workup

  1. temperatureunder reflux overnight
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7ae107ef36c34414a3255deee1d15a25
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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