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

HRID 1112019Notes

Reaction equation

HRID 1112019 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-8814bdfdad734bd9817417a991b3ebab
Source dataset
uspto-grants-1978_10
Patent number
US04119775

Reaction notes

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