Water → 5-Nitro-2-quinolinemethanol

HRID 2215435Notes

Reaction equation

HRID 2215435 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-d544850119a544d78164b27d7a6f88a3
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

Loading…