Ethanol → 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid

HRID 2295725ノート

反応式

HRID 2295725 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17]CC)=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:21].C(O)C.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:21]

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10404195ethyl 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate

生成物 1

HCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid収率 91.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Six hundred mg (1.83 mmol) of ethyl 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylate obtained in Example 15 was added to a mixed solvent of ethanol and water (1:1), then 2 ml of 2 N aqueous solution of sodium hydroxide was added thereto, and the mixture was heated to reflux for two hours. When the reaction was completed, ethanol was evaporated therefrom, the residual aqueous solution was adjusted to pH nearly 7.0 with 1 N aqueous solution of acetic acid and, after stirring for a while, crystals separated out therefrom were collected by filtration, successively washed with ethanol, acetone and ether and air dried to give 501 mg (91.4 percent) of the title compound, melting point 318° C. (decomposition). Elementary analysis calculated as C12H7FClNO3S: C 48.09, H 2.35, N. 4.67; Found: C 48.28, H 2.14, N 4.37.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for two hours
  3. customethanol was evaporated
  4. customseparated out
  5. filtrationtherefrom were collected by filtration
  6. washsuccessively washed with ethanol, acetone and ether and air
  7. customdried

出典と根拠

ORDレコード
ord-0f23ade7236f4960a96ab9ab7d482156
出典データセット
uspto-grants-1984_01
特許番号
US04426381

反応ノート

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