Formaldehyde → HCID 178519804, compound

HRID 2105992Notes

Reaction equation

HRID 2105992 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH-:12].[Na+].[CH2:14]=O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:14][OH:12]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 178516385quinolin-4-ol

Product 1

HCID 178519804HCID 178519804, compound

Conditions

Temperature
45 °C

Procedure

A mixture of 4-hydroxyquinoline (5.0 g), aqueous sodium hydroxide solution (1M, 42 mL) and formaldehyde solution (37% in water, 6 mL) was heated at 45° C. for 18.5 hours. The reaction mixture was filtered, acidified with 2N HCl (21 mL) and extracted with ethyl acetate. The aqueous layer was chilled to afford 4-hydroxy-3-hydroxymethylquinoline (2.0 g) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with ethyl acetate
  3. temperatureThe aqueous layer was chilled

Sources & evidence

ORD record
ord-88bb20ce648f48e3b7953c67f5e37b76
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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