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

HRID 462069Notes

Reaction equation

HRID 462069 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-ad0ffb70444c49afbb975c05fc633956
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

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