Benzene → HCID 13533222, compound

HRID 2397561Notes

Reaction equation

HRID 2397561 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4].[NH:17]1[CH2:22][CH2:21]OCC1.[CH:23]1C=CC=C[CH:24]=1>>[CH:22]([NH:17][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4])([CH2:23][CH3:24])[CH3:21]

Participants

4

Reactant 3

HCID 241BenzeneHCID 8083MorpholineHCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 13533222HCID 13533222, compound

Procedure

10 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) prepared in Example 4 or 8 was suspended in 60 ml of benzene, and 9 ml of morpholine was added to the suspension followed by allowing the mixture to react while heating under refluxing and stirring for 4 hours. The reaction mixture was cooled and the resulting precipitate was filtered. The precipitate was dissolved in 60 ml of isopropanol and the solution was adjusted to a pH of 2- 3 with concentrated hydrochloric acid. The resulting acidic solution was cooled with ice and the precipitate formed was filtered followed by recrystallization from ethanol. The precipitate was dissolved in 20 ml of water and the solution was adjusted to a pH 7.5- 8.0 with sodium bicarbonate and ice-cooled. The precipitate formed upon cooling was filtered and recrystallized from ethanol to obtain 4.2 g of white amorphous 5-morpholinoacetyl-8-hydroxycarbostyril (II) having a melting point of 238° - 239.5° C. (with decomposition). The product thus obtained was confirmed by IR and NMR spectral analyses and elemental analysis.

Workup

  1. customto react
  2. temperaturewhile heating
  3. temperatureunder refluxing
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe resulting precipitate was filtered
  6. dissolutionThe precipitate was dissolved in 60 ml of isopropanol
  7. temperatureThe resulting acidic solution was cooled with ice
  8. customthe precipitate formed
  9. filtrationwas filtered
  10. customfollowed by recrystallization from ethanol
  11. dissolutionThe precipitate was dissolved in 20 ml of water
  12. temperaturecooled
  13. customThe precipitate formed
  14. temperatureupon cooling
  15. filtrationwas filtered
  16. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6cdf335b6ed04ea38068b02170915531
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

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