Dimethylformamide → Methyl 6-morpholinonicotinate

HRID 550277Notes

Reaction equation

HRID 550277 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 2776466Methyl 6-morpholinonicotinateYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 6-chloronicotinate (1.02 g, 5.93 mmol), morpholine (0.57 ml, 6.52 mmol), potassium carbonate (1.06 g, 7.71 mmol) and DMF (20 ml) was stirred at 100° C. for 6 hrs. The reaction mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and concentrated under reduced pressure. The obtained solid was collected by filtration and washed with diisopropy ether to give the title compound (0.93 g, 71%) as a colorless powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe obtained solid was collected by filtration
  7. washwashed with diisopropy ether

Sources & evidence

ORD record
ord-539fd1eee098444a86bc1cbb26602466
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

Loading…