Morpholine → HCID 13138484, compound

HRID 27881Notes

Reaction equation

HRID 27881 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4](Cl)[N:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(O)C>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 131384822,6-Dichloro-4-phenylnicotinonitrile

Product 1

HCID 13138484HCID 13138484, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 24.9 gm (0.1 mol) of 2,6-dichloro-4-phenyl-3-cyano-pyridine in 400 ml of ethanol was slowly admixed with 17.4 gm (0.2 mol) of morpholine, and the resulting mixture was refluxed for about two hours. Even while refluxing, but primarily upon subsequent cooling (optionally on an ice water bath) of the reaction mixture, a colorless crystalline precipitate formed which was collected by suction filtration, very thoroughly washed with water and dried. 25.8 gm (86% of theory) of 2-chloro-6-morpholino-4-phenyl-3-cyano-pyridine, m.p. 198°-200° C., were obtained.

Workup

  1. temperaturethe resulting mixture was refluxed for about two hours
  2. temperatureEven while refluxing
  3. temperatureprimarily upon subsequent cooling (optionally on an ice water bath) of the reaction mixture
  4. customa colorless crystalline precipitate formed which
  5. filtrationwas collected by suction filtration
  6. washvery thoroughly washed with water
  7. customdried

Sources & evidence

ORD record
ord-149a632815854c328bc2cb7a97769d1e
Source dataset
uspto-grants-1980_09
Patent number
US04224322

Reaction notes

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