Morpholine → 2-Morpholino-5-nitropyridine

HRID 56149

Reaction equation

HRID 56149 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CCN(CC)CC>CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 968722-Morpholino-5-nitropyridineYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5-nitropyridine (3.17 g, 20 mmol), morpholine (2.00 g, 23 mmol) and Et3N (2.43 g, 24 mmol) in EtOAc (200 mL) was refluxed for 3 h, then cooled to rt, and washed with water (100 mL×3). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (3.89 g, 93%).

Workup

  1. temperaturewas refluxed for 3 h
  2. washwashed with water (100 mL×3)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d36d0a8ce77342ad813c302e60c1030e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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