Hydrochloric Acid → 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone

HRID 2209542ノート

反応式

HRID 2209542 の反応式
[C:1]([CH:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[C:14]2[C:13](=[O:24])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:26]([F:29])([F:28])[F:27])[OH:25])([O:3]CC)=[O:2].O.[OH-].[Li+].Cl>C(O)C.O>[C:1]([CH:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[C:14]2[C:13](=[O:24])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:26]([F:28])([F:29])[F:27])[OH:25])([OH:3])=[O:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 199589273-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone

生成物 1

HCID 154912663-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone収率 84.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
90 °C

実験手順

A suspension of 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5(1H )-quinolone (3.39 g) in ethanol (20 ml) and water (20 ml) was treated with lithium hydroxide monohydrate (0.75 g). The mixture was heated at 90° C. for 1.5 hours, diluted with water, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed (water and brine), dried, filtered, and evaporated to yield a foam which was purified by chromatography (ethyl acetate and ethyl acetate/methanol, 3:1) to afford 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (2.67 g ) as a pale yellow foam; MS: m/z=381(m).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed (water and brine)
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a foam which
  7. customwas purified by chromatography (ethyl acetate and ethyl acetate/methanol, 3:1)

出典と根拠

ORDレコード
ord-3855cba814404ed7abbe5540e4ba8c22
出典データセット
uspto-grants-1995_10
特許番号
US05455253

反応ノート

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