Hydrochloric Acid → Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate

HRID 637916Notes

Reaction equation

HRID 637916 reaction equation
N1CCCCC1.[CH2:7]([O:9][C:10](=[O:15])[CH2:11][C:12](O)=O)[CH3:8].[CH3:16][C:17]1[N:22]=[CH:21][C:20](C=O)=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1>[CH2:7]([O:9][C:10](=[O:15])[CH:11]=[CH:12][C:20]1[CH:21]=[N:22][C:17]([CH3:16])=[CH:18][CH:19]=1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 70615Monoethyl malonateHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 54365744Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoateYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.5 ml of piperidine are added to a solution of 25 g (0.19 mole) of malonic acid monoethyl ester in 50 ml of pyridine, followed by the dropwise addition of 17 g (0.14 mole) of 6-methyl-3-pyridine aldehyde. The mixture is refluxed for 5 hours and, after cooling, is poured onto a mixture of ice and concentrated hydrochloric acid. After extraction by shaking with diethyl ether, the organic phase is dried over sodium sulfate and concentrated by evaporation in vacuo, leaving 17.8 g (67%) of the title compound in the form of an oil which is further processed without purification.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureafter cooling
  3. extractionAfter extraction
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-5a97337189ab41b98183f198bc21154e
Source dataset
uspto-grants-1985_12
Patent number
US04559344

Reaction notes

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