2-Chlorobenzaldehyde → HCID 54101000, compound

HRID 894649Notes

Reaction equation

HRID 894649 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([O:12][CH:13]([O:22][CH2:23][CH3:24])[C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:11]>N1CCCCC1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:15]([C:14]([CH:13]([O:12][CH2:10][CH3:11])[O:22][CH2:23][CH3:24])=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 69962-ChlorobenzaldehydeHCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 54101000HCID 54101000, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2-chlorobenzaldehyde (1.0543 g), ethyl 4,4-diethoxyacetoacetate (1.6477 g) and piperidine (1 to 2 drop(s)) in benzene (30 ml) was refluxed under azeotropic dehydration for 4.5 hours. After cooling, the resultant solution was washed with water and dried. The solvent was removed from the solution to give orange oil (2.7196 g) of ethyl 2-(2-chlorobenzylidene)-4,4-diethoxyacetoacetate. The mixture of the compound obtained above and ethyl 3-amino-4,4-diethoxycrotonate (1.6580 g) was heated with stirring at about 100° C. for 1.5 hours and about 120° C. for 8 hours. After cooling, the reaction mixture was dissolved in ethyl acetate. The solution was washed with water and dried, and then the solvent was removed from the solution to give orange oil (4.21 g) of diethyl 2,6-bis(diethoxymethyl)-4-(2-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. The product was purified by a column chromatography on silica gel with an eluant (benzene:ethyl acetate=10:1) to give pure product.

Workup

  1. temperatureAfter cooling
  2. washthe resultant solution was washed with water
  3. customdried
  4. customThe solvent was removed from the solution

Sources & evidence

ORD record
ord-cc65c8c591504f1ca60444abbd8e3692
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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