Sodium Chloride → 6-Hydroxymethylquinoline

HRID 569737Notes

Reaction equation

HRID 569737 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](OCC)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[Na+]>CCOCC>[OH:12][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 946706-Quinolinecarboxylic acid, ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15143856-Hydroxymethylquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

59.5 g (0.296 mole) of ethyl quinoline-6-carboxylate are stirred in 970 ml of ether at -70° C. with 750 ml (0.9 mole) of diisobutylaluminum hydride (DIBAL, 20% strength in toluene, 1.2 molar) overnight. The temperature is then allowed to rise to -35° C. and 310 ml of sodium chloride solution are added, whereupon the temperature slowly comes to 20° C. The mixture is stirred at 20° C. for 3 hours and the aluminum hydroxide is filtered off with suction and rinsed with ether/ethyl acetate. The organic phase is washed with 100 ml of sodium chloride solution, dried over Na2SO4 and evaporated. Crude yield: 40 g

Workup

  1. customto rise to -35° C.
  2. customslowly comes to 20° C
  3. filtrationthe aluminum hydroxide is filtered off with suction
  4. washrinsed with ether/ethyl acetate
  5. washThe organic phase is washed with 100 ml of sodium chloride solution
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-2977ff07bdda4262b3dd201fcfc11bd3
Source dataset
uspto-grants-1988_03
Patent number
US04734407

Reaction notes

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