Water → 4-Hydroxyquinoline-3-carbaldehyde

HRID 2166880Notes

Reaction equation

HRID 2166880 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]([C:12]#N)=[CH:2]1.[PH2]([O-])=[O:15].[Na+].O.N1C=CC=CC=1>C(O)(=O)C.[Ni]>[CH:12]([C:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][CH:2]=1)=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 35393493-Quinolinecarbonitrile, 4-hydroxy-HCID 178527019HCID 178527019, compound

Product 1

HCID 3481374-Hydroxyquinoline-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The 4-(1H)-quinolone-3-nitrile (12 g) and sodium hypophosphite (16.12 g) were dissolved in a mixture of acetic acid:water:pyridine=125 ml: 125 ml:250 ml and 4 g of Raney Nickel (W2 grade) added (Backeberg and Staskim, J.C.S. 1962, 3691). The reaction mixture was heated at 60° C. for four hours, then the hot suspension was filtered and the catalyst cake washed with warm ethanol into the filtrates. The combined filtrates and washings were evaporated to one-third of the original volume and on equal volume of water added. The precipitated solid was filtered off, washed with water and dried to give the required 3-formyl compound as a light-brown solid, m.p. 268°-270° C. (3-formyl-4(1H)-quinolone).

Workup

  1. filtrationthe hot suspension was filtered
  2. washthe catalyst cake washed with warm ethanol into the filtrates
  3. customThe combined filtrates and washings were evaporated to one-third of the original volume and on equal volume of water
  4. additionadded
  5. filtrationThe precipitated solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ed2bee7108794984b52290f90c41b884
Source dataset
uspto-grants-1983_06
Patent number
US04390541

Reaction notes

Loading…