Water → 7-(Benzyloxy)isoquinoline

HRID 1940567Notes

Reaction equation

HRID 1940567 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[CH2:14]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 4597677-Isoquinolinol

Product 1

HCID 211924457-(Benzyloxy)isoquinolineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxyisoquinoline (prepared by the method of R. B. Woodward and W. D. Doering, J. Am. Chem. Soc., 1945, 67, 860) (1.45 g, 10 mmol) in DMF (20 ml) was added sodium hydride (60% dispersion in oil, 0.4 g, 10 mmol) portionwise. After stirring for 30 minutes, benzyl bromide (1.2 ml, 10 mmol) was added and the reaction mixture stirred for 2 h. The reaction mixture was poured into water and extracted with diethyl ether (3×100ml). The ether extracts were combined, washed with 2N sodium hydroxide solution (2×50 ml), brine (50 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give the title compound (1.6 g, 68%); δH (CDCl3) 5.21 (2H, s, OCH2), 7.30-7.51 (7H, m, ArH), 7.59 (1H, d, J 8.3 Hz, ArH), 7.75 (1H, d, J 13 Hz, ArH), 8.42 (1H, d, J 8 Hz, ArH), and 9.14 (1H, s, ArH).

Workup

  1. stirringthe reaction mixture stirred for 2 h
  2. extractionextracted with diethyl ether (3×100ml)
  3. washwashed with 2N sodium hydroxide solution (2×50 ml), brine (50 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2c7d6bf5d688468d8709236d64ff6ac7
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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