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

HRID 602378Notes

Reaction equation

HRID 602378 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(OCC)(=O)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>[Cl-].[Na+].O>[O:21]1[CH2:22][CH2:23][N:18]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 2762487Methyl 2-(morpholin-4-yl)pyridine-4-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2-chloroisonicotinate (320 mg, 1.89 mmol) was dissolved in morpholine (5 mL) and stirred at 90° C. for 4 hours. The reaction mixture was added with saturated brine and ethyl acetate, and the organic layer was separated, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain methyl 2-morpholinoisonicotinate (50 mg, 98%).

Workup

  1. customthe organic layer was separated
  2. washby washing with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-1f40cf3cefd44fb68ab4f6ad9bca8d43
Source dataset
uspto-grants-2011_03
Patent number
US07906522B2

Reaction notes

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