Morpholine → 4-Morpholino-2-nitrobenzonitrile

HRID 1431245Notes

Reaction equation

HRID 1431245 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1COCC1>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 969244-Chloro-2-nitrobenzonitrile

Product 1

HCID 134992654-Morpholino-2-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-chloro-2-nitrobenzonitrile (2.0 g, 11 mmol) in THF (40 mL) was added morpholine (1.0 g, 11 mmol). The reaction was heated at reflux overnight. After this time the reaction was cooled to rt and then it was partitioned between EtOAc (150 mL) and NaHCO3 (50 mL, satd aq. solution). The separated organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:1) gave 4-morpholino-2-nitrobenzonitrile.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customit was partitioned between EtOAc (150 mL) and NaHCO3 (50 mL, satd aq. solution)
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9b10deb16b3e47efb2cf95c1b8f87c24
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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