Acetic Acid → Isopropyl 2-phenyl-4-quinolone-6-carboxylate

HRID 986239

Reaction equation

HRID 986239 reaction equation
N[C@H:2]([CH:7]=O)[CH2:3]CSC.[C:9]1([C:15]2[CH2:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:26]([OH:28])=[O:27])[CH:21]=3)[N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C>C(O)(C)C>[C:9]1([C:15]2[CH2:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:26]([O:28][CH:2]([CH3:7])[CH3:3])=[O:27])[CH:21]=3)[N:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 446793Methionin ALHCID 704325112-Phenyl-4-quinolone-6-carboxylic acid

Product 1

HCID 70432651Isopropyl 2-phenyl-4-quinolone-6-carboxylateYield 78.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Metal sodium (0.33 gram) is dissolved in 40 ml of anhydrous isopropyl alcohol and the solution is heated to reflux for one hour with 2 grams of the 2-phenyl-4-quinolone-6-carboxylic acid obtained in Example 2. After cooling, the solution is mixed with ice water, acidified with acetic acid, the crystals which separate out therefrom are collected by filtration. The crystals are washed with water, washed with methanol, and dried to give 0.6 gram of isopropyl 2-phenyl-4-quinolone-6-carboxylate, colorless powder, melting at above 300° C.

Workup

  1. temperaturethe solution is heated
  2. temperatureAfter cooling
  3. customthe crystals which separate out
  4. filtrationtherefrom are collected by filtration
  5. washThe crystals are washed with water
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-ec7b457643e94d7f8fa23723661d1b4e
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Linked notes

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