Water → 6-Hydroxyquinoline-5-carbaldehyde

HRID 1789385Notes

Reaction equation

HRID 1789385 reaction equation
[OH-:1].[Na+].[OH2:3].O[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2.[CH:15](Cl)(Cl)Cl>>[OH:1][C:5]1[CH:14]=[CH:13][C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]=1[CH:15]=[O:3]

Participants

5

Reactant 4

HCID 962WaterHCID 6212Chloroform2×HCID 113746-HydroxyquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 135600936-Hydroxyquinoline-5-carbaldehyde

Conditions

Temperature
90 °C

Procedure

Sodium hydroxide (25 g.) was dissolved in 35 ml. of water with cooling, 6-hydroxyquinoline (5 g.) in 15 ml. of chloroform was added and the reaction mixture heated to reflux (about 90° C.) for 12 hours, during which two further 15 ml. portions of chloroform were added - one after 2 hours and the other after 6 hours. The reaction mixture was cooled and crude product recovered by filtration. The crude was dissolved in 125 ml. of hot water treated with activated carbon, filtered hot, cooled and acidified with acetic acid and filtered to yield title product [2.5 g.; m.p. 136°-137° C.; m/e 173; pnmr/ CDCl shows aldehyde proton at 10.5 ppm and aromatic protons at 7.2-9.4 ppm⟧

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationcrude product recovered by filtration
  4. dissolutionThe crude was dissolved in 125 ml
  5. additionof hot water treated with activated carbon
  6. filtrationfiltered hot
  7. temperaturecooled
  8. filtrationfiltered

Sources & evidence

ORD record
ord-88edf4562ff1434b84869e91d827f11b
Source dataset
uspto-grants-1987_08
Patent number
US04689336

Reaction notes

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