Hydrochloric Acid → rac-Ethyl 5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875329ノート

反応式

HRID 875329 の反応式
[CH2:1](O)[CH3:2].Cl.[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:28])=[C:10]([CH2:12][CH2:13][NH:14][CH:15]2[CH2:24][CH2:23][CH2:22][C:21]3[N:20]=[C:19]([C:25]([OH:27])=[O:26])[CH:18]=[CH:17][C:16]2=3)[CH:11]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[F:5][C:6]1[CH:7]=[CH:8][C:9]([OH:28])=[C:10]([CH2:12][CH2:13][NH:14][CH:15]2[CH2:24][CH2:23][CH2:22][C:21]3[N:20]=[C:19]([C:25]([O:27][CH2:1][CH3:2])=[O:26])[CH:18]=[CH:17][C:16]2=3)[CH:11]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 89940808rac-5-{[2-(5-Fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid

生成物 1

HCID 89950549rac-Ethyl 5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

40 ml of anhydrous ethanol and 4 ml of a 4 N solution of hydrogen chloride in dioxane were added to 1.93 g (5.84 mmol) of rac-5-{[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid, and the mixture was stirred under reflux overnight. The reaction solution was then cooled to room temperature, and first ethyl acetate and then, slowly, saturated aqueous sodium bicarbonate solution were added. The organic phase was separated off, dried over magnesium sulphate, filtered and concentrated to dryness. This gave 1.67 g (4.66 mmol, 80% of theory) of the target compound.

後処理

  1. temperatureunder reflux overnight
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-23e6f81139c14a3cbc8ac2e452e68d7f
出典データセット
uspto-grants-2015_03
特許番号
US08981104B2

反応ノート

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