3-Chlorobenzaldehyde → HCID 69071615, compound

HRID 890151Notes

Reaction equation

HRID 890151 reaction equation
[NH2:1]/[C:2](/[CH3:11])=[CH:3]\[C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5].[C:12]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=O>CC(O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:13]([C:12]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:14]([CH3:16])[NH:1][C:2]([CH3:11])=[C:3]2[C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5])[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 142266Benzyl acetoacetateHCID 136714102-Cyanoethyl 3-aminocrotonate

Product 1

HCID 69071615HCID 69071615, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.53 g (22.9 mmol) of 2-cyanoethyl 3-aminocrotonate, 4.40 g (22.9 mmol) of benzyl acetoacetate and 2.60 ml (23.0 mmol) of 3-chlorobenzaldehyde were heated at 80° C. under stirring in 100 ml of 2-propanol for 3 days. 2-Propanol was evaporated under reduced pressure to obtain 5-benzyl 3-(cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. 100 ml of ethyl acetate and 10% palladium/carbon were added to the reaction mixture, and they were stirred at room temperature in hydrogen atmosphere under atmospheric pressure for 7 days. The reaction liquid was filtered. The filtrate was evaporated under reduced pressure. The residue was washed with chloroform to obtain the title compound.

Workup

  1. custom2-Propanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ad909f1c955141ce946e829f1b06b6f1
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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