Ethanol → 3-Phenyl-quinoline-5-carboxylic acid

HRID 2372821Notes

Reaction equation

HRID 2372821 reaction equation
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-])=O)[C:4](=[O:5])[O:3]1.[CH2:15](O)[CH3:16]>[Pd].S([O-])([O-])(=O)=O.[Ba+2]>[C:6]1([C:15]2[CH:16]=[N:12][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:11]=3[CH:2]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 110955283-hydroxy-4-nitro-3H-isobenzofuran-1-one

Product 1

HCID 109886653-Phenyl-quinoline-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 16218511Pd barium sulfateCatalyst

Procedure

50 g (0.256 mol) of 3-hydroxy-4-nitro-phthalide are hydrogenated at 20° C. and at 3 bar using 5 g of Pd/barium sulphate (5%) in 380 ml of ethanol. The mixture is filtered with suction, and 0.308 mol=38.7 ml of phenylacetaldehyde solution are added to the filtrate. The mixture is boiled for 4 hours, the quinolinecarboxylic acid precipitating. It is cooled, filtered with suction and washed with ethanol 28.3 g (44.3% of theory) of a colorless compound of melting point>290° C. are obtained.

Workup

  1. customare hydrogenated at 20° C. and at 3 bar
  2. filtrationThe mixture is filtered with suction, and 0.308 mol=38.7 ml of phenylacetaldehyde solution
  3. additionare added to the filtrate
  4. temperatureIt is cooled
  5. filtrationfiltered with suction
  6. washwashed with ethanol 28.3 g (44.3% of theory) of a colorless compound of melting point>290° C.
  7. customare obtained

Sources & evidence

ORD record
ord-eddabf8758c345a9824ae054a7c9f5cd
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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