2,2'-[5-(1-Hydroxy-1-(3-pyridyl]methyl)-1,3-phenylene]di(2-methyl propiononitrile) → 2,2'-[5-(3-Pyridylmethyl)-1,3-phenylene]di(2-methylpropiononitrile)

HRID 2107773Notes

Reaction equation

HRID 2107773 reaction equation
O[CH:2]([C:9]1[CH:10]=[C:11]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])[CH:12]=[C:13]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])[CH:14]=1)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1>ClCCl.S(Cl)(Cl)=O>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][C:9]2[CH:10]=[C:11]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])[CH:12]=[C:13]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])[CH:14]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 193494362,2'-[5-(1-Hydroxy-1-(3-pyridyl]methyl)-1,3-phenylene]di(2-methyl propiononitrile)

Product 1

HCID 193494102,2'-[5-(3-Pyridylmethyl)-1,3-phenylene]di(2-methylpropiononitrile)

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of the product from Example 34 (50 mg) in dichloromethane (2 ml) and thionyl chloride (0.1 ml) was heated under reflux for 1 h, then evaporated to dryness under reduced pressure. The residue was dissolved in ethanol, 10% palladium-on-carbon catalyst was added, and the mixture was shaken in an atomosphere of hydrogen at room temperature and atmospheric pressure for 1 h. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure, and the residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate. The ethyl acetate phase was separated, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography, eluting with ethyl acetate, to give 2,2'-[5-(3-pyridylmethyl)-1,3 -phenylene]di(2-methylpropiononitrile), mp 82°-84°.

Workup

  1. temperatureunder reflux for 1 h
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol
  4. addition10% palladium-on-carbon catalyst was added
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated to dryness under reduced pressure
  7. customthe residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate
  8. customThe ethyl acetate phase was separated
  9. customdried
  10. customevaporated to dryness under reduced pressure
  11. customthe residue was purified by flash column chromatography
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1a939b29f8e8450ebf882bb45c615987
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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