Isopropanol → Methyl 2-(morpholin-4-yl)pyridine-4-carboxylate

HRID 1838249Notes

Reaction equation

HRID 1838249 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[CH:17](O)(C)C>>[O:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([O:7][CH3:17])=[O:6])[CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8083MorpholineHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2762487Methyl 2-(morpholin-4-yl)pyridine-4-carboxylate

Conditions

Temperature
150 °C

Procedure

A 5.0 g portion of 2-chloroisonicotinic acid and 6.91 g of morpholine were suspended in 16 ml of isopropanol and stirred at 150° C. for 27 hours in a sealed tube. The solvent was evaporated and then the residue was mixed with 70 ml of methanol and 5 ml of concentrated sulfuric acid and heated under reflux for 6.5 hours. The solvent was evaporated and the residue was dissolved in chloroform and washed with saturated aqueous sodium bicarbonate. After evaporation of the solvent, the resulting mixture was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (4:1, v/v) to obtain 4.42 g of crystals of the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was mixed with 70 ml of methanol and 5 ml of concentrated sulfuric acid
  3. temperatureheated
  4. temperatureunder reflux for 6.5 hours
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in chloroform
  7. washwashed with saturated aqueous sodium bicarbonate
  8. customAfter evaporation of the solvent
  9. washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-1374b52180f84e949afd156745550029
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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