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

HRID 1713792Notes

Reaction equation

HRID 1713792 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O>[Cl:8][C:7]1[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 594643324-(3-Chloro-5-nitropyridin-2-yl)morpholine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2,3-Dichloro-5-nitropyridine (Synthesis, 1990, 6, 499-501) (20 g, 104 mmol) was added portionwise to morpholine (40 mL) at 0° C. and heated at 120° C. for 1 h. The reaction was cooled to room temperature, water (100 mL) added and the reaction extracted with DCM (3×150 mL). The organics were dried (MgSO4), filtered, and the solvent removed under reduced pressure to give the product as a yellow solid, which was triturated with isohexane and allowed to dry under vacuum at 60° C. 1H NMR δ 8.98 (1H, d), 8.47 (1H, d), 3.74-3.69 (4H, m), 3.67-3.62 (4H, m); MS m/e MH+ 244.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe reaction extracted with DCM (3×150 mL)
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-dacb9b83f06b4d3c8e177744629618cb
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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