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

HRID 1160158Notes

Reaction equation

HRID 1160158 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 formate are added. The mixture is left stirring at 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-fbb5667110c548b9a1086ed6abc19804
Source dataset
uspto-grants-2010_10
Patent number
US07816368B2

Reaction notes

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