Potassium Hydroxide → 3-Tert.butyl-4-phenyl isoquinoline hydrochloride

HRID 46814Notes

Reaction equation

HRID 46814 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([Cl:21])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[H][H]>[Pd].C(O)C>[ClH:21].[C:1]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 203858433-Tert.butyl-1-chloro-4-phenyl isoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 203858553-Tert.butyl-4-phenyl isoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 21.7 g. (0.073 mole) of 3-tert.butyl-1-chloro-4-phenyl isoquinoline, 4.09 g. (0.073 mole) potassium hydroxide, 1.09 g 10% palladium on carbon and 1 liter of ethanol is hydrogenated at room temperature and 50 psi until 1 equivalent of hydrogen is absorbed. The catalyst is filtered off and washed with ethanol, combined ethanol portions are evaporated in vacuo. The residue is dissolved in ethyl ether, washed with water, dried, and filtered and the filtrate treated with gaseous HCl. The resulting white solid is filtered and recrystallized from ethanolethyl ether, washed with water, dried, and filtered and the filtrate treated with gaseous HCl. The resulting white solid is filtered and recrystallized from ethanol-ethyl ether (1:1) to give 3-tert.butyl-4-phenyl isoquinoline hydrochloride; m.p. 236°-238° C.

Workup

  1. additionA mixture of 21.7 g
  2. customis hydrogenated at room temperature
  3. filtrationThe catalyst is filtered off
  4. washwashed with ethanol
  5. customare evaporated in vacuo
  6. dissolutionThe residue is dissolved in ethyl ether
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. additionthe filtrate treated with gaseous HCl
  11. filtrationThe resulting white solid is filtered
  12. customrecrystallized from ethanolethyl ether
  13. washwashed with water
  14. customdried
  15. filtrationfiltered
  16. additionthe filtrate treated with gaseous HCl
  17. filtrationThe resulting white solid is filtered
  18. customrecrystallized from ethanol-ethyl ether (1:1)

Sources & evidence

ORD record
ord-f75499ac04ce451bbe59d2d5cc63ef1c
Source dataset
uspto-grants-1979_11
Patent number
US04175191

Reaction notes

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