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Acetic Acid → Diethyl 2-ethyl-4-[2-(4-chlorobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4660
Notes
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Reaction equation

HRID 4660 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH:9]=O.[C:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=O)[CH2:19][CH3:20].[NH:28]1CCC[CH2:30][CH2:29]1.[C:34]([OH:37])(=[O:36])[CH3:35].[CH:38]1C=CC=C[CH:39]=1>>[CH2:19]([C:18]1[NH:28][C:29]([CH3:30])=[C:35]([C:34]([O:37][CH2:38][CH3:39])=[O:36])[CH:9]([C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 241BenzeneHCID 8082PiperidineHCID 78656Ethyl 3-oxovalerateHCID 198462802-(4-Chlorobutoxy)-5-nitrobenzaldehyde

Product 1

HCID 14050494Diethyl 2-ethyl-4-[2-(4-chlorobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Procedure

In 106 ml of dry benzene were dissolved 13.0 g of 2-(4-chlorobutoxy)-5-nitrobenzaldehyde, 7.28 g of ethyl propionylacetate, 0.20 ml of piperidine and 0.62 ml of acetic acid, and the solution was refluxed for 9 hours while removing water using a Dean-Stark trap. After cooling the reaction solution, 6.52 g of ethyl 3-aminocrotonate was added to the solution, and the mixture was refluxed under heating for 11 hours. After cooling the mixture, precipitated crude crystals were collected by filtration, and recrystallized from methanol to give 13.13 g of diethyl 2-ethyl-4-[2-(4-chlorobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. temperaturethe solution was refluxed for 9 hours
  2. customwhile removing water using a Dean-Stark trap
  3. temperatureAfter cooling the reaction solution, 6.52 g of ethyl 3-aminocrotonate
  4. additionwas added to the solution
  5. temperaturethe mixture was refluxed
  6. temperatureunder heating for 11 hours
  7. temperatureAfter cooling the mixture
  8. customprecipitated crude crystals
  9. filtrationwere collected by filtration
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f9daf0c7d744415583c393b130452832
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04727082

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes