Dimethyl Sulfoxide → 4-(6-Nitropyridin-3-yl)morpholine

HRID 1262289Notes

Reaction equation

HRID 1262289 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C.CS(C)=O>>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 8471TriethylamineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholineYield 81%

Conditions

Temperature
80 °C

Procedure

Into a 8-dram vial, 5-Bromo-2-nitro-pyridine (2.00 g, 9.85 mmol), Morpholine (1.12 g, 12.8 mmol), Triethylamine (1.37 mL, 9.85 mmol) and Dimethyl sulfoxide (10 mL, 100 mmol) were added. The reaction mixture was heated at 80° C. overnight. The reaction was cooled to RT and poured over ice. The solid was filtered and washed with water. The solid was washed with ethanol. The resulting solid was dried under vacuum to give 4-(6-Nitro-pyridin-3-yl)-morpholine as a white solid (1.60 g, 81%).

Workup

  1. temperatureThe reaction was cooled to RT
  2. additionpoured over ice
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. washThe solid was washed with ethanol
  6. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-8b2358178b8c4eadbb3c2f50933af739
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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