Acetic Acid → 1-Ethyl-4-hydroxy-6-methylquinolin-2(1H)-one

HRID 462067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462067
[CH2:1]([NH:3][C:4]1[C:5](=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[C:6](O)=[O:7])[CH3:2].[C:14](OC(=O)C)(=O)[CH3:15].C(O)(=[O:23])C>>[CH2:14]([N:3]1[C:4]2[C:5](=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[C:6]([OH:7])=[CH:2][C:1]1=[O:23])[CH3:15]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 125113262-(Ethylamino)-5-methylbenzoic acid

Produkt 1

HCID 546963011-Ethyl-4-hydroxy-6-methylquinolin-2(1H)-one

Versuchsvorschrift

N-Ethyl-5-methyl anthranilic acid (17.6g -- 0.098 mole; m.p. 159° C) was refluxed in acetic acid (43 ml) and acetic anhydride (43 ml) for 12 hrs. The dark red solution was cooled and poured onto crushed ice. The mixture was made alkaline, filtered off tarry material and neutralised with hydrochloric acid. The yellow crystalline product was filtered off, washed well with water and recrystallised from ethanol, m.p. 275°-280° (Found- C, 70,87; H, 6.34; N, 7.17 C12H13NO2 requires; C, 70.88; H, 6.44; N, 6.89%).

Aufarbeitung

  1. temperatureThe dark red solution was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationfiltered off tarry material
  5. filtrationThe yellow crystalline product was filtered off
  6. washwashed well with water
  7. customrecrystallised from ethanol, m.p. 275°-280° (Found- C, 70,87; H, 6.34; N, 7.17 C12H13NO2 requires; C, 70.88; H, 6.44; N, 6.89%)

Quellen und Nachweise

ORD-Eintrag
ord-1d5814519f9a4fec8d0eb9c8edc67542
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065457

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