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Methyl acetoacetate → dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4669
Notes
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Reaction equation

HRID 4669 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH: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]([O:24][CH3:25])(=[O:23])[CH2:19][C:20]([CH3:22])=O.[NH2:26]/[C:27](/[CH3:33])=[CH:28]\[C:29]([O:31][CH3:32])=[O:30]>C(O)(C)C>[Cl:1][CH2:2]/[CH:3]=[CH: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]1[C:19]([C:18]([O:24][CH3:25])=[O:23])=[C:20]([CH3:22])[NH:26][C:27]([CH3:33])=[C:28]1[C:29]([O:31][CH3:32])=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 140504962-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde

Product 1

HCID 14050497dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 48.8%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

5.2 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde, 2.4 g of methyl acetoacetate and 2.3 g of methyl 3-aminocrotonate was dissolved in 30 ml of iso-propanol, and the solution obtained was refluxed for 3.5 hours under heating. After cooling, the precipitated crystals were collected by filtration to give 4.4 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. (mp. 206°-207° C.). The product obtained was used directly for the next process without purification.

Workup

  1. customthe solution obtained
  2. temperaturewas refluxed for 3.5 hours
  3. temperatureunder heating
  4. temperatureAfter cooling
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-062c826e74c641139e59148b875c82f5
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