HCID 59338811, compound → HCID 59338817, compound

HRID 12581Notes

Reaction equation

HRID 12581 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[CH:11][C:8]=2C#N)[CH2:3][CH2:2]1>OS(O)(=O)=O.O>[C:15]1([C:13]2[N:14]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=[CH:11][C:12]=2[C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 59338811HCID 59338811, compound

Product 1

HCID 59338817HCID 59338817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-morpholino-6-phenyl-5-p-tolylnicotinonitrile (Compound 116,120 mg, 0.3 mmol) in 50% H2SO4 (5 ml) was heated at 140° C. overnight. The mixture was cooled down to room temperature and diluted with water, extracted with CH2Cl2. The organic layer was washed with water and brine, dried over MgSO4, concentrated in vacuo and purified by MPLC column chromatography (silica gel, 25% ethyl acetate in hexane) to provide the title compound as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by MPLC column chromatography (silica gel, 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2ecc3c987ef342dcaf56a896c2b14bed
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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