Morpholine → 5-Morpholino-3-nitropicolinonitrile

HRID 1431253Notes

Reaction equation

HRID 1431253 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CS(C)=O.CCOC(C)=O.O>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 596311815-Morpholino-3-nitropicolinonitrile

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-bromo-3-nitropicolinonitrile (5.0 g, 22 mmol) in DMSO (30 mL) was added morpholine (3.8 mL, 44 mmol). The reaction was stirred at rt for 2 h. After this time the reaction was diluted with EtOAc (300 mL) and water (100 mL). The separated organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting solid was washed with MeOH (15 mL) to give 5-morpholino-3-nitropicolinonitrile. Mass Spectrum (ESI) m/e=235.2 (M+1).

Workup

  1. dry with materialThe separated organic layer was dried over magnesium sulfate
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. washThe resulting solid was washed with MeOH (15 mL)

Sources & evidence

ORD record
ord-7875bbf571af4a04a992a86f4dcb6a59
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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