2-Chlorobenzaldehyde → HCID 178469200, compound

HRID 489306Notes

Reaction equation

HRID 489306 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]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:17]([C:16]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:20])[NH:10][C:11]2=[N:12][NH:13][CH:14]=[C:15]12

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 8868Ethyl AcetoacetateHCID 178418806HCID 178418806, compound

Product 1

HCID 178469200HCID 178469200, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chlorobenzaldehyde (1.7 g), 3-aminopyrazole (1.0 g) and ethyl acetoacetate (1.6 g) in acetonitrile (20 mL) was heated under reflux overnight. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure to give an oil. The oil was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (8:2)) to give the title compound (850 mg) as colorless crystals.

Workup

  1. temperatureunder reflux overnight
  2. customthe solvent was evaporated under reduced pressure
  3. customto give an oil
  4. customThe oil was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (8:2))

Sources & evidence

ORD record
ord-95a9597a6f634b9cbedaf728f7b9e5a2
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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