Potassium Hydroxide → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1194106Notes

Reaction equation

HRID 1194106 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH2:7]2.[OH-].[K+]>O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 29203356-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (41 g) was dissolved in H2O, basified with aqueous KOH solution and extracted with CHCl3. The CHCl3 extracts were dried over MgSO4 and evaporated to dryness to yield 33 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline base (0.2M). The base (33 g, 0.2M) and Palladium Black (1.5 g) were mixed together and heated at 160°-190° C. for 6 hours. The cooled reaction mixture was extracted with MeOH and the Palladium Black was filtered off. The MeOH was evaporated to dryness and the residue was chromatographed in CHCl3 on silica gel column. Fractions containing product were combined and evaporated to yield 6-methoxyisoquinoline as an oil (16 g, 50%).

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe CHCl3 extracts were dried over MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-321f867b8fc241308a5348e7039ccb40
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

Loading…