Acetonitrile → Ethyl 6-morpholinonicotinate

HRID 2228593Notes

Reaction equation

HRID 2228593 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(#N)C>O>[N:13]1([C:2]2[N:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8083MorpholineHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 14297054Ethyl 6-morpholinonicotinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 6-chloronicotinate (5.0 g) and morpholine (10 ml) were mixed and then heated to 100° C. In less than 5 minutes at this temperature, a thick paste formed. Acetonitrile (15 ml) was added and heating was continued overnight at 90° C. The mixture was cooled, diluted with water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo to give ethyl 6-morpholin-4-ylpyridine-3-carboxylate as a white solid. NMR (300 MHz, CDCl3: 8.80 (s, 1H), 8.05 (d, 1H), 6.60 (d, 1H), 4.35 (q, 2H), 3.80 (m, 4H), 3.65 (m, 4H), 1.35 (t, 3H).

Workup

  1. waitIn less than 5 minutes at this temperature
  2. customa thick paste formed
  3. temperatureheating
  4. temperatureThe mixture was cooled
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b634127504ca40c3b7ae2f51dc4c5d4b
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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