2-Chlorobenzaldehyde → HCID 54101000, compound

HRID 1164576Notes

Reaction equation

HRID 1164576 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 (21.8240 g) 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 3-aminocrotonate (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-8eb8ab33182a4a9983eb3b212476d7df
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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