Water → 3-benzylisoquinoline

HRID 2390024Notes

Reaction equation

HRID 2390024 reaction equation
[C:1]([C:9]1[N:10]=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+].O>C(O)CO>[CH2:1]([C:9]1[N:10]=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12777809HCID 12777809, compound

Product 1

HCID 27529323-benzylisoquinolineYield 98.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

303 mg of 3-benzoyl isoquinoline and 9.75 g of hydrazine hydrate were dissolved in 10 mL of ethylene glycol at room temperature, followed by stirring at 150° C. After 10 minutes, to the reaction liquid was added 3.65 g of pulverized potassium hydroxide, followed by warming to 180° C. and continuously reacting for additional 2 hours. After completion of the reaction, the reaction liquid was left to be cooled, and water was added thereto, followed by extraction with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (diethyl ether:n-hexane=1:1) to obtain 280 mg (yield 95%) of a title compound as a light yellow solid.

Workup

  1. customto the reaction liquid
  2. temperatureby warming to 180° C.
  3. waitcontinuously reacting for additional 2 hours
  4. customAfter completion of the reaction
  5. customthe reaction liquid
  6. waitwas left
  7. temperatureto be cooled
  8. extractionfollowed by extraction with diethyl ether
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified

Sources & evidence

ORD record
ord-a05e7d4c3c7a4e18adbaafb4485590d7
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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