3-Bromoquinoline → HCID 21459047, compound

HRID 2254804Notes

Reaction equation

HRID 2254804 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])CCC.[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][C:26]=1[O:33][CH3:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[OH:30])=[CH:27][C:26]=1[O:33][CH3:34])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 214133-BromoquinolineHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 21459047HCID 21459047, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 25.0 g of 3-bromoquinoline is dissolved in 200 ml of dry ether and cooled to -60°. At this temperature there are added dropwise within 15 minutes 75.1 ml of a 1.6 molar solution of n-butyllithium, whereupon the mixture is stirred for 10 minutes. A solution of 26.5 g of vanillin benzyl ether in 250 ml of dry ether is added dropwise thereto at -60°, the mixture is subsequently stirred at room temperature of 3 hours, poured into about 1.5 l of ice-water and extracted three times with 600 ml of ethyl acetate each time. The organic phase is washed with water, dried over sodium sulfate and evaporated. The resulting oil is chromatographed on 1 kg of silica gel with methylene chloride/ethyl acetate (1:1). The crystalline crude product obtained is recrystallized form ethyl acetate. There is obtained α-[4-(benzyloxy)-3-methoxyphenyl]-3-quinolinemethanol in the form of colourless crystals of m.p. 124°-125°.

Workup

  1. temperaturecooled to -60°
  2. stirringat -60°, the mixture is subsequently stirred at room temperature of 3 hours
  3. extractionextracted three times with 600 ml of ethyl acetate each time
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe resulting oil is chromatographed on 1 kg of silica gel with methylene chloride/ethyl acetate (1:1)
  8. customThe crystalline crude product obtained
  9. customis recrystallized form ethyl acetate

Sources & evidence

ORD record
ord-60d1b2597a934bd2897ddac304de0820
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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