Hydrochloric Acid → Methyl 3-hydroxy-2-(4-pyridinyl)propenoate

HRID 272645Notes

Reaction equation

HRID 272645 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11]C)=[O:9])=[CH:3][CH:2]=1.[H-].[Na+].[CH:15](OCC)=[O:16].Cl>C1(C)C=CC=CC=1.CCOC(C)=O.CCOCC>[OH:16][CH:15]=[C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 736321Ethyl pyridine-4-acetate

Product 1

HCID 136378429Methyl 3-hydroxy-2-(4-pyridinyl)propenoate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

9 g of ethyl 2-(4-pyridinyl)acetate and 1.35 g of 95% NaH are mixed in 90 ml of toluene. The mixture is heated at 100° C. for 30 minutes and is then cooled, and 8.8 ml of ethyl format are added. The mixture is left stirring at for 1 hour and at 100° C. for 45 minutes. The reaction medium is cooled and then 25.5 ml of 2N HCl are added. Filtration is carried out and then the precipitate formed is taken up in AcOEt and then in ether to produce 5.65 g of the expected compound.

Workup

  1. temperatureis then cooled
  2. waitThe mixture is left
  3. temperatureThe reaction medium is cooled
  4. filtrationFiltration
  5. customthe precipitate formed

Sources & evidence

ORD record
ord-36832878d9ce471987c586db0fd8d3fa
Source dataset
uspto-grants-2008_11
Patent number
US07456193B2

Reaction notes

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