Water → (Quinolin-5-yl)methanol

HRID 633766Notes

Reaction equation

HRID 633766 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17](OC)=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[N:7]1[C:16]2[C:11](=[C:12]([CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12503486Methyl quinoline-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 823080(Quinolin-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 171 mg (4.49 mmol) of lithium aluminum hydride in 20 ml of THF is cooled to 0° C. A solution of 700 mg (3.74 mmol) of methyl quinoline-5-carboxylate in 5 ml of THF is then added dropwise. The reaction mixture is stirred at 0° C. for 1 hour and then hydrolysed with, in this order, 0.17 ml of H2O, 0.17 ml of NaOH and 3×0.17 ml of H2O. The precipitate formed is filtered off and washed with THF and then with EtOAc. The organic phase is washed with saturated NaCl solution, dried and evaporated. After purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol are obtained, corresponding to the following characteristics:

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with THF
  4. washThe organic phase is washed with saturated NaCl solution
  5. customdried
  6. customevaporated
  7. customAfter purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol
  8. customare obtained, corresponding to the following characteristics

Sources & evidence

ORD record
ord-15ef336b9597444780de8985a44941ef
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

Loading…