Sodium Carbonate → Ethyl 2-[(2,6-dichloropyridin-3-yl)oxy]propanoate

HRID 1833828Notes

Reaction equation

HRID 1833828 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([O:12][C:13](=[O:17])[CH:14](Br)[CH3:15])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:10]([O:12][C:13](=[O:17])[CH:14]([O:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:9])=[CH:5][CH:6]=1)[CH3:15])[CH3:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 1043172,6-Dichloropyridin-3-ol

Product 1

HCID 12906172Ethyl 2-[(2,6-dichloropyridin-3-yl)oxy]propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

164 g (1 mole) of 2,6-dichloro-3-pyridinol, 1500 ml of acetonitrile, 253.4 g (1.4 moles) of 2-bromopropionic acid ethyl ester and 127.2 (1.2 moles) of sodium carbonate are refluxed for 3 hours. The reaction mixture is then cooled, filtered, and concentrated in a rotary evaporator. The residue is taken up in ether and washed with 2N sodium hydroxide solution. After drying with magnesium sulphate, the solution is concentrated by evaporation and distilled in vacuo; a clear oil distills at 110°-140°/0.1 torr; yield: 200 g; i nD25 : 1.5200. Crystallisation from benzene/petroleum ether yields a product having a melting point of 41°-46°;

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationfiltered
  3. concentrationconcentrated in a rotary evaporator
  4. washwashed with 2N sodium hydroxide solution
  5. dry with materialAfter drying with magnesium sulphate
  6. concentrationthe solution is concentrated by evaporation
  7. distillationdistilled in vacuo
  8. distillationa clear oil distills at 110°-140°/0.1 torr
  9. customCrystallisation from benzene/petroleum ether
  10. customyields a product

Sources & evidence

ORD record
ord-db033275ae1c4f3d9b39317c9890a1a2
Source dataset
uspto-grants-1978_01
Patent number
US04067725

Reaction notes

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