Hydrogen chloride-ethyl acetate → HCID 67536949, compound

HRID 2383044Notes

Reaction equation

HRID 2383044 reaction equation
[C:1]([C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:16][C:17]#[N:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:19].CCOC(C)=O>[Pt]=O.CCO>[ClH:19].[CH3:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:18][CH2:17][CH2:16]2

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59396527HCID 59396527, compound

Product 1

HCID 67536949HCID 67536949, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To (2-benzoyl-3-methylphenyl)acetonitrile (3.3 g) were added EtOH (40 mL), 4 M HCl/EtOAc (5 mL), and platinum oxide (IV) (0.53 g), followed by stirring under a hydrogen atmosphere for 5 hours. The reaction liquid was filtered through celite and then concentrated. Toluene was added to the concentrate, followed by extraction with an aqueous 1 M HCl solution. A 28% aqueous ammonia solution was added to the aqueous layer, which was then extracted with toluene and dried over magnesium sulfate. The solvent was evaporated and the residue was dissolved in toluene to which 4 M HCl/EtOAc (5 mL) was then added, followed by concentration. iPrOH and diisopropyl ether were added to the resulting residue, and the precipitated solid was collected to obtain 8-methyl-1-phenyl-3,4-dihydroisoquinoline hydrochloride (1.5 g).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through celite
  3. concentrationconcentrated
  4. additionToluene was added to the concentrate
  5. extractionfollowed by extraction with an aqueous 1 M HCl solution
  6. additionA 28% aqueous ammonia solution was added to the aqueous layer, which
  7. extractionwas then extracted with toluene
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. dissolutionthe residue was dissolved in toluene to which 4 M HCl/EtOAc (5 mL)
  11. additionwas then added
  12. concentrationfollowed by concentration
  13. additioniPrOH and diisopropyl ether were added to the resulting residue
  14. customthe precipitated solid was collected

Sources & evidence

ORD record
ord-527d9e4f7b1443aea47aab1f102c3d5b
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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