2-Chlorobenzaldehyde → HCID 178468899, compound

HRID 489418Notes

Reaction equation

HRID 489418 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]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)[CH:17]([CH3:19])[CH3:18].C(=O)([O-])O.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:16]([CH:17]([CH3:19])[CH3:18])[NH:10][C:11]2=[N:12][NH:13][CH:14]=[C:15]12

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 81583Ethyl isobutyrylacetateHCID 516892Sodium BicarbonateHCID 178418806HCID 178418806, compound

Product 1

HCID 178468899HCID 178468899, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chlorobenzaldehyde (1.41 g), 3-aminopyrazole (0.83 g) and ethyl isobutyrylacetate (1.58 g) were stirred in acetic acid (10 ml) at 80° C. for 2 hours. Under ice-cooling, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The insoluble material was filtered off, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1)). The purified product was crystallized from hexane-ethyl acetate to give the title compound (115 mg) as white crystals.

Workup

  1. temperatureUnder ice-cooling
  2. filtrationThe insoluble material was filtered off
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1))
  8. customThe purified product was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4af1c7d3360c4cfdb4837ec992dacc55
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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