Water → 5-Nitro-2-quinolinemethanol

HRID 2054977Notes

Reaction equation

HRID 2054977 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:14]=[O:15])=[N:9]2)([O-:3])=[O:2].O1CCCC1.[BH4-].[Na+].O>CO>[OH:15][CH2:14][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 47370745-nitroquinoline-2-carbaldehyde

Product 1

HCID 49133605-Nitro-2-quinolinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (3.46 mmol) of 5-nitroquinoline-2-carbaldehyde are dissolved in 13 ml of methanol and 7.0 ml of tetrahydrofuran and mixed at 0° C. with 523 mg (13.9 mmol) of sodium borohydride. After 5 hours, the reaction is brought to a halt by adding water. The solvent is removed in a vacuum, the residue is taken up in dichloromethane and water, the aqueous phase is extracted with dichloromethane, and the combined organic phases are dried on sodium sulfate. After the solvent is removed, and after purification on silica gel with hexane-ethyl acetate (0-100%), 390 mg (55% of theory) of the product is obtained.

Workup

  1. customThe solvent is removed in a vacuum
  2. extractionwater, the aqueous phase is extracted with dichloromethane
  3. customthe combined organic phases are dried on sodium sulfate
  4. customAfter the solvent is removed
  5. customafter purification on silica gel with hexane-ethyl acetate (0-100%), 390 mg (55% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-e9d48223b7994188a205152e6792673d
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

Loading…