2-chloro-7-methylquinoline-3-carbaldehyde → (2-chloro-7-methylquinolin-3-yl)methanol

HRID 726641Notes

Reaction equation

HRID 726641 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([CH3:16])=[CH:9][CH:10]=2)[N:5]=1>C(O)C.O1CCCC1>[Cl:3][C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([CH3:16])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 7761842-chloro-7-methylquinoline-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 828414(2-chloro-7-methylquinolin-3-yl)methanolYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6.9 g (180 mmol) of sodium borohydride in 250 ml of absolute ethanol, a solution of 15 g (73 mmol) of 2-chloro-3-formyl-7-methylquinoline in 250 ml of dry tetrahydrofuran was added over 15 minutes without cooling. During the addition a slight H2 -evolution and a temperature rise to +28° C. was observed. The reaction mixture was stirred at room temperature for 4 hours and then 4 ml of the reaction mixture was evaporated in vacuo and the residue dissolved in ethyl acetate, extracted with saturated sodium hydrogen carbonate solution, dried over sodium sulfate and evaporated in vacuo to give a residue of 100 mg. 1H-NMR indicated complete conversion to the alcohol. After 5 hours the whole reaction mixture was worked up in the same way to give 14.8 g 2-chloro-3-hydroxymethyl-7-methylquinoline after evaporation.

Workup

  1. temperaturewithout cooling
  2. additionDuring the addition a slight H2 -evolution
  3. customto +28° C.
  4. custom4 ml of the reaction mixture was evaporated in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate
  6. extractionextracted with saturated sodium hydrogen carbonate solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customto give a residue of 100 mg
  10. customAfter 5 hours the whole reaction mixture

Sources & evidence

ORD record
ord-3568f2f8be2842acbbe5fd4d9a56e3ad
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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