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

HRID 1658100Notes

Reaction equation

HRID 1658100 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+]>>[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

4

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

Procedure

5-Chloro-N-methyl anthranilic acid (15g; 0.081 mole) was dissolved in acetic 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 solution 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; C10H8NClO 2 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-cf1af9cfb9be41ccb8880157580b1482
Source dataset
uspto-grants-1976_06
Patent number
US03962445

Reaction notes

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