Morpholine → 4-(5-Chloro-3-nitropyridin-2-yl)morpholine

HRID 1431378Notes

Reaction equation

HRID 1431378 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](F)=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 122757685-Chloro-2-fluoro-3-nitropyridine

Product 1

HCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-chloro-2-fluoro-3-nitropyridine (5 g, 28 mmol) in THF (40 mL) was added morpholine (4 mL, 42 mmol). The reaction was stirred at 0° C. for ten min, at rt for 1 h, and refluxed for four h. The reaction was then cooled to rt, taken up in EtOAc, and washed with satd aq. sodium bicarbonate and brine. The organic layer was dried (magnesium sulfate) and concentrated, affording 4-(5-chloro-3-nitropyridin-2-yl)morpholine as a yellow oil. Mass Spectrum (ESI) m/e=244.0 (M+1).

Workup

  1. temperaturerefluxed for four h
  2. temperatureThe reaction was then cooled to rt
  3. washwashed with satd aq. sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-947a7104fc6143e9a402bcbce6dcbf96
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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