Sodium Bicarbonate → HCID 86745775, compound

HRID 1195818Notes

Reaction equation

HRID 1195818 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH2:7][C:6]2=[O:14])#N.C(C1C=C2C(=CC=1)N=C(C)C=C2[OH:28])#N.C(=O)(O)[O-].[Na+]>[Ni].C(O)=O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH2:7][C:6]2=[O:14])=[O:28]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 67789301HCID 67789301, compoundHCID 178428837HCID 178428837, compound

Product 1

HCID 86745775HCID 86745775, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 6-cyano-2methyl-4-quinolone (9.2 g, Chem. Abs., 51, 11347h; known therein as 6-cyano-4-hydroxyquinaldine), Raney nickel (10 g) and 75% formic acid (150 ml ) was heated at reflux for 3 hours. The mixture was cooled, neutralised with a saturated aqueous solution of sodium bicarbonate and filtered. The solid residue was washed with warm methanol (3×50 ml). The combined filtrates were extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (100 ml), dried over sodium sulphate and evaporated to give 6-formyl-2-methyl-4-quinolone as a fawn coloured solid (9.3 g).

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe solid residue was washed with warm methanol (3×50 ml)
  5. extractionThe combined filtrates were extracted with ethyl acetate (3×50 ml)
  6. washThe combined extracts were washed with water (100 ml)
  7. dry with materialdried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9c83970805c040ecaf9d305349a73291
Source dataset
uspto-grants-1992_05
Patent number
US05112837

Reaction notes

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