2-Hydroxyquinoline-3-carbaldehyde → 3-(Hydroxymethyl)-1,2-dihydroquinolin-2-one

HRID 2225324Notes

Reaction equation

HRID 2225324 reaction equation
[CH:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 5893342-Hydroxyquinoline-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27645783-(Hydroxymethyl)-1,2-dihydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

34 Grams of 3-formylcarbostyril was suspended in 800 ml of methanol, and 7.4 g of sodium borohydride was added gradually thereto under ice-cooled condition with stirring. The reaction mixture was further stirred under ice-cooling for 3 hours. The precipitated crystals were collected by filtration and recrystallized from methanol to obtain 33.2 g of 3-hydroxymethylcarbostyril in the form of colorless prism-like crystals.

Workup

  1. temperatureunder ice-cooled condition
  2. stirringThe reaction mixture was further stirred under ice-
  3. temperaturecooling for 3 hours
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-232010b97b334f3ba4c89924066305b9
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Reaction notes

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