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

HRID 462069ノート

反応式

HRID 462069 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-ad0ffb70444c49afbb975c05fc633956
出典データセット
uspto-grants-1977_12
特許番号
US04065457

反応ノート

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