Potassium Hydroxide → HCID 68519611, compound

HRID 639884Notes

Reaction equation

HRID 639884 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH3:20])[N:3]=1.[OH-].[K+]>CCO.[Pd]>[Cl-:1].[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[NH+:3][C:4]([CH3:20])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86041352HCID 86041352, compound

Product 1

HCID 68519611HCID 68519611, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-chloro-6-methoxy-3-methyl-4-phenylisoquinoline (0.55 g) in 25 mL EtOH was treated with 120 mg KOH and 30 mg Pd—C (10%). The reaction was shaken under an H2 atmosphere (50 psi) for 20 h. The reaction was filtered through celite and concentrated to dryness, then dissolved in isopropanol and treated with excess HCl. Crystallization from isopropanol/diethyl ether gave the titled compound.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated to dryness
  3. dissolutiondissolved in isopropanol
  4. additiontreated with excess HCl
  5. customCrystallization from isopropanol/diethyl ether

Sources & evidence

ORD record
ord-77c8c0b27d0944a981e9368c50bdee5f
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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