Acetone → HCID 71118729, compound

HRID 633840Notes

Reaction equation

HRID 633840 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]=[O:16])=[CH:11][C:10]([O:17][CH3:18])=[CH:9][CH:8]=2.CC(C)=O.ClCCl>C(O)C.CO>[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][OH:16])=[CH:11][C:10]([O:17][CH3:18])=[CH:9][CH:8]=2

Participants

7

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 86027543HCID 86027543, compound

Product 1

HCID 71118729HCID 71118729, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (2.09 g, 55.2 mmol, 1.0 eq) is added portionwise at 0° C. to a stirred suspension of (3-chloro-6-methoxy-quinolin-4-yl)-acetaldehyde (13.0 g, 55.2 mmol, 1.0 eq) in ethanol (200 mL). After 1 hour stirring at 0° C., acetone (50 mL) is added to quench the reaction. Solvents are removed and the resulting crude product is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 2-(3-chloro-6-methoxy-quinolin-4-yl)-ethanol as a yellow solid (13.1 g, 99% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. customSolvents are removed
  4. customthe resulting crude product is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-7865de9125dc41fbbadca418203300bd
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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