Acetic Anhydride → 6-Chloro-4-hydroxy-1-methylquinolin-2(1H)-one

HRID 462069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462069
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH:11][CH3:12])=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]([CH3:12])[C:13](=[O:15])[CH:14]=[C:7]2[OH:9]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 125113245-Chloro-2-(methylamino)benzoic acid

Produkt 1

HCID 546962916-Chloro-4-hydroxy-1-methylquinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5-Chloro-N-methyl anthranilic acid (15g; 0.081 mole) was dissolved in acetic acid (41 ml) and acetic anhydride (41 ml) and the dark mixture refluxed for 12 hours. After cooling the red solution was poured onto crushed ice, basified with 2.5N sodium hydroxide and filtered free of tar. The filtrate on acidification to pH5 gave the carbostyril as a yellow solid, m.p. (AcOH) 317°-318° C (Found; C, 57.39; H, 3.98; N, 6.83; Cl, 16.69; C10H8NClO2 requires C, 57.29; H, 3.85; N, 6.68; Cl, 16.91%).

Aufarbeitung

  1. temperatureAfter cooling the red solution
  2. additionwas poured
  3. customonto crushed ice
  4. filtrationfiltered free of tar

Quellen und Nachweise

ORD-Eintrag
ord-ad0ffb70444c49afbb975c05fc633956
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065457

Notizen zur Reaktion

Wird geladen…