Potassium Hydroxide → 6-Methoxy-1-methyl-3,4-dihydroisoquinoline

HRID 275895Notes

Reaction equation

HRID 275895 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12](=O)[CH3:13])[CH:6]=[CH:7][CH:8]=1.[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:12]([CH3:13])=[N:11][CH2:10][CH2:9]2

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 10330235N-[2-(3-methoxyphenyl)ethyl]acetamide

Product 1

HCID 138591866-Methoxy-1-methyl-3,4-dihydroisoquinolineYield 93.4%

Conditions

Temperature
110 °C

Procedure

A mixture soultion of polyphosphoric acid (61.4 ml, 0.66 mol) and phosphorouspentoxide(28.0 g, 0.2 mol) was heated to 90° C. N-(3-methoxyphenylethyl) acetamide (63.6 g, 0.33 mol) was added to the mixture solution and then stirred for 2 hours at 110° C. The reaction mixture was poured into ice water, adjusted to alkali with potassium hydroxide, and then extracted with ethyl ether. The extract was dried over anhydrous magnesium sulfate and concentrated under a reduces pressure. The resulting residue was purified by a silica gel column chromatography, using a solution of methanol and dichloromethane (1:20) as a eluent, to give 54.0 g of the titled compound.

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under a reduces pressure
  4. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-02fafa00edc44bb78611cf51bfbf954a
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

Loading…