Quinaldic Acid → 1-(Quinolin-2-yl)ethan-1-one

HRID 325296Notes

Reaction equation

HRID 325296 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][Li]>O1CCCC1>[C:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:13])[CH3:14]

Participants

4

Reactant 2

HCID 7124Quinaldic AcidHCID 178418348HCID 178418348, compound

Product 1

HCID 3187031-(Quinolin-2-yl)ethan-1-oneYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Quinaldic acid (2.76 grams, 0.017 mole) was dissolved in 100 ml of dried tetrahydrofuran. Then 25 ml of 1.6 M (0.04 mole) of methyl lithium was added using a syringe. Reaction appeared immediate. The solution was stirred and heated under reflux for two hours and then poured into 600 ml of ice water. The ketone (2-acetylquinoline) was extracted with four 25 ml portions of ethyl ether which, after drying, was removed by rotary evaporation to yield ca. 1.0 g (ca. 40%) of 2-acetylquinoline.

Workup

  1. customReaction
  2. temperatureheated
  3. temperatureunder reflux for two hours
  4. extractionThe ketone (2-acetylquinoline) was extracted with four 25 ml portions of ethyl ether which
  5. customafter drying
  6. customwas removed by rotary evaporation

Sources & evidence

ORD record
ord-8e603d5c5f644adf84f0b4b685ac973e
Source dataset
uspto-grants-1984_04
Patent number
US04440771

Reaction notes

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