Chloroacetic Acid → (4-Oxoquinolin-1(4H)-yl)acetic acid

HRID 1729637Notes

Reaction equation

HRID 1729637 reaction equation
O.O.O.[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.Cl[CH2:16][C:17]([OH:19])=[O:18]>[OH-].[K+]>[N:8]1([CH2:16][C:17]([OH:19])=[O:18])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:4])[CH:6]=[CH:7]1

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 178526978HCID 178526978, compound

Product 1

HCID 22766108(4-Oxoquinolin-1(4H)-yl)acetic acidYield 17.2%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

4-Hydroxyquinoline trihydrate (20 g., 0.2 mole) is dissolved in a 50% aqueous potassium hydroxide solution and chloroacetic acid (20 g., 0.2 mole) is incrementally added. The resulting solution is heated at its reflux temperature for 18 hours, chilled, acidified and filtered to give 7 g of 4-quinolone-1-acetic acid having a m.p. 278°-279° C.

Workup

  1. additionis incrementally added
  2. temperatureThe resulting solution is heated at its
  3. temperaturereflux temperature for 18 hours
  4. temperaturechilled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bdfbed800e2d4f0e9cc11605a65dd50a
Source dataset
uspto-grants-1976_11
Patent number
US03989687

Reaction notes

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