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Hydrochloric Acid → 3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine 3,5-dicarboxylate

HRID 890150
Notes
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Reaction equation

HRID 890150 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH2:18][C:19]#[N:20])=[O:15])=[C:12]([CH3:21])[NH:11][C:10]([CH:22](OC)[O:23]C)=[C:9]2[C:27]([O:29][CH2:30][CH:31]=[CH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:28])[CH:5]=[CH:6][CH:7]=1.Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH2:18][C:19]#[N:20])=[O:15])=[C:12]([CH3:21])[NH:11][C:10]([CH:22]=[O:23])=[C:9]2[C:27]([O:29][CH2:30][CH:31]=[CH:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:28])[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 695899473-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-dimethoxylmethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 743481133-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine 3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

1.82 g (3.38 mmol) of 3-(3-phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-dimethoxylmethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate was dissolved in 12.7 ml of acetone. 1.27 ml of 6 N hydrochloric acid was added to the obtained solution, and they were stirred at 0° C. for 6 hours. Acetone was evaporated under reduced pressure, and then water was added to the residue. After the extraction with chloroform, the organic layer was successively washed with a saturated aqueous sodium hydrogencarbonate solution and saturated aqueous salt solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1) to obtain the title compound.

Workup

  1. customAcetone was evaporated under reduced pressure
  2. additionwater was added to the residue
  3. extractionAfter the extraction with chloroform
  4. washthe organic layer was successively washed with a saturated aqueous sodium hydrogencarbonate solution and saturated aqueous salt solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-25fb0ce6d8a24b0abadc7aac46fd4a79
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06995179B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes