Ammonium Hydroxide → 5-(Hydroxymethyl)quinolin-8-ol

HRID 2259542Notes

Reaction equation

HRID 2259542 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.[NH4+].[OH-:16]>O>[OH:16][CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 6757865-(Hydroxymethyl)quinolin-8-olYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 ml Ehrlenmeyer flask with a magnetic stirrer, 23 grams (0.1 moles) of 5-chloromethyl-8-hydroxyquinoline hydrochloride and 200 ml of H2O were stirred, producing a bright yellow solution. NH4OH (7.0 grams; 0.2 moles) in concentrated form was added slowly. The color of the solution changed to amber. As the pH approached neutral, the color disappeared, and a precipitate formed. The precipitate was filtered, washed with water, and oven dried at 105° C. After drying, 15.2 grams (87% yield) of product was left.

Workup

  1. customproducing a bright yellow solution
  2. customa precipitate formed
  3. filtrationThe precipitate was filtered
  4. washwashed with water, and oven
  5. customdried at 105° C
  6. customAfter drying

Sources & evidence

ORD record
ord-29471843545442f4b58edaba064de95a
Source dataset
uspto-grants-1995_12
Patent number
US05474827

Reaction notes

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