Acetic Acid → HCID 15284565, compound

HRID 861921Notes

Reaction equation

HRID 861921 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[C:5]([O:20][CH3:21])[CH:6]=[CH:7][C:8]=2[O:18][CH3:19])[N:3]=1.C(O)(=[O:24])C>>[C:12]1([C:11]2[C:2](=[O:24])[NH:3][C:4]3[C:9]([CH:10]=2)=[C:8]([O:18][CH3:19])[CH:7]=[CH:6][C:5]=3[O:20][CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 5329282HCID 5329282, compound

Product 1

HCID 15284565HCID 15284565, compoundYield 100%

Procedure

A solution of 2-chloro-3-phenyl-5,8-dimethoxyquinoline (200 mg, 0.67 mmol) was refluxed for 3 hours in acetic acid (1.5 ml) and water (0.05 ml.) After the solvent was evaporated, the residue was dissolved in water, basified with aqueous ammonium hydroxide 25% and extracted with chloroform (3×25 ml). The combined chloroform layers were dried over sodium sulfate and evaporated, yielding an essentially pure residue of 187 mg (100%) of 3-phenyl-5,8-dimethoxy-2-(1H)-quinolinone. m.p. 207 (CDCl3).

Workup

  1. customwater (0.05 ml.) After the solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with chloroform (3×25 ml)
  4. dry with materialThe combined chloroform layers were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-75883db318704bfeacf079de8a3db1ef
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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