Morpholine → 2-Morpholino-5-nitrobenzonitrile

HRID 1744501Notes

Reaction equation

HRID 1744501 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 74104812-Morpholino-5-nitrobenzonitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitrobenzonitrile (16.7 g) and morpholine (16 g) were added to ethanol (300 ml) and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give 5-nitro-2-morpholinobenzonitrile (19.7 g), melting point: 138–140° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionDiisopropyl ether was added to the residue
  3. customcrystallization
  4. customThe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-f7f86a5b36e946f0b2e7cb27807bdb9d
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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