Phenol → 6-Methoxy-7-methyl-1-phenoxyisoquinoline

HRID 1366753Notes

Reaction equation

HRID 1366753 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+].[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[CH3:12])[C:2]([O:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:3][CH:4]=[CH:5]2

Participants

6

Reactant 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 537828801-Chloro-6-methoxy-7-methylisoquinoline

Product 1

HCID 669417846-Methoxy-7-methyl-1-phenoxyisoquinolineYield 19.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1-chloro-6-methoxy-7-methyl-isoquinoline (9 g, 43.48 mol), phenol (16.3 g), potassium hydroxide (9.45 g) and xylene (100 ml) was refluxed for 4 days. The reaction mixture was poured out into aqueous sodium hydroxide (4 M) and the xylene layer separated. The aqueous layer was extracted twice with toluene. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give a residue. The residue was purified by flash chromatography using dichloromethane gave 6-methoxy-7-methyl-1-phenoxyisoquinoline (9 g, 33.96 mmol).

Workup

  1. temperaturewas refluxed for 4 days
  2. customthe xylene layer separated
  3. extractionThe aqueous layer was extracted twice with toluene
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f69c57d012bd4562b8f92e58c39a4652
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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