2-Chlorobenzaldehyde → HCID 54101000, compound

HRID 614581Notes

Reaction equation

HRID 614581 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 3

HCID 69962-ChlorobenzaldehydeHCID 8082PiperidineHCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 54101000HCID 54101000, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(2)-(1) A solution of 2-chlorobenzaldehyde (14.0570 g), ethyl 4,4-diethoxyacetoacetate (21.8240g) and piperidine (1 ml) in benzene (100 ml) was refluxed under azeotropic dehydration for 4 hours. The resultant solution was washed with water, dried and concentrated to give oily ethyl 2-(2-chlorobenzylidene)-4,4-diethoxyacetoacetate. The mixture of the compound obtained above and ethyl 3aminocrotonate (12.92 g) was heated in an oil bath (about 100° C.) for 8 hours. The reaction mixture was dissolved in ethyl acetate, washed with water, dried and then the solvent was removed to give crude oil (52.4 g). The oil was purified by column chromatography on silica gel with an eluent (benzene:ethyl acetate = 20:1) to give diethyl 2-methyl-4-(2-chlorophenyl)-6-diethoxymethyl-1.4-dihydropyridine-3,5-dicarboxylate, which was recrystallized from n-hexane to give the pure crystals (20.2445 g), m.p. 75° to 77° C.

Workup

  1. washThe resultant solution was washed with water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-93f4f15eda8d401190ab2baa5c7081ed
Source dataset
uspto-grants-1979_03
Patent number
US04145432

Reaction notes

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