Hydrochloric Acid → HCID 178471091, compound

HRID 1719544Notes

Reaction equation

HRID 1719544 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 20267136Ethyl 3-(2-methoxypyridin-4-yl)propanoate

Product 1

HCID 178471091HCID 178471091, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl β-(2-methoxy-4-pyridyl)propionate (89.1 g) and ethanolic HCl (200 ml) were stirred under reflux in ethanol (900 ml) for 48 hours. The reaction mixture was evaporated under reduced pressure to give an oily residue which was dissolved in water (300 ml). This solution was taken to pH9 with potassium carbonate solution and extracted into ethyl acetate (6×250 ml). The combined ethyl acetate extracts were washed with water, dried over MgSO4 and evaporated under reduced pressure to afford an oil which solidified to give white crystals of ethyl β-(2-hydroxy-4-pyridyl)propionate which were washed with petroleum ether (40°-60°) and dried in vacuo (59.58 g), m.p. 73°-76.5° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto give an oily residue which
  3. extractionextracted into ethyl acetate (6×250 ml)
  4. washThe combined ethyl acetate extracts were washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customto afford an oil which

Sources & evidence

ORD record
ord-9d05fd57b0564072b897aae3854b0a7e
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

Loading…