HCID 23159744, compound → ethyl 5-hydroxyquinoline-3-carboxylate

HRID 1011424Notes

Reaction equation

HRID 1011424 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[N:14]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[N:14]2

Participants

4

Reactant 1

HCID 23159744HCID 23159744, compound

Product 1

HCID 135618214ethyl 5-hydroxyquinoline-3-carboxylateYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

210 mg (0.68 mmol) of compound prepared in stage B dissolved in 25 mL of ethanol was stirred in presence of Pd/C5% (75 mg, 0.034 mmol) under an atmosphere of hydrogen for 3 hours. The palladium was then removed by filtration and ethanol was evaporated under reduced pressure. The 1H NMR of the crude product showed a part of a reduced by-product at the pyridine ring (dihydroquinoline derivatives). The mixture was dissolved in ethanol and treated with air gas until complete re-oxidation of the product. Evaporation of the solvent gave 135 mg (yield: 91%) of compound of molecular formula C12H11NO3. Aspect: yellow powder.

Workup

  1. customThe palladium was then removed by filtration and ethanol
  2. customwas evaporated under reduced pressure
  3. dissolutionThe mixture was dissolved in ethanol
  4. additiontreated with air gas until complete re-oxidation of the product
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0cc5bf39712843f3a1246f369c8571fd
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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