Ethanol → HCID 86634793, compound

HRID 1972156Notes

Reaction equation

HRID 1972156 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:19])=[N:11][CH:12]=[C:13]([C:17]=2[CH3:18])[C:14]([OH:16])=[O:15])[CH:5]=[CH:4][N:3]=1.[CH2:20](O)[CH3:21].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:19])=[N:11][CH:12]=[C:13]([C:17]=2[CH3:18])[C:14]([O:16][CH2:20][CH3:21])=[O:15])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 866347925-(2-Chloropyridin-4-yloxy)-4,6-dimethylnicotinic acid

Product 1

HCID 86634793HCID 86634793, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A three necked round bottom flask containing 5-(2-chloropyridin-4-yloxy)-4,6-dimethylnicotinic acid (11.7 g, 42.0 mmol) was charged with ethanol (250 mL), benzene (300 mL) and sulphuric acid (10 mL). The flask was fitted with Dean Stark apparatus and the reaction stirred at reflux overnight. The solution was cooled and carefully neutralized with saturated NaHCO3 solution. The material was extracted with EtOAc, dried, and concentrated to afford the title compound (8.6 g, 67%) as an oil which solidified to a white solid upon standing in a refrigerator (4° C.) overnight.

Workup

  1. customThe flask was fitted with Dean Stark apparatus
  2. temperatureat reflux overnight
  3. temperatureThe solution was cooled
  4. extractionThe material was extracted with EtOAc
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6a33e9504705492690d1985adc3148a1
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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