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

HRID 54459노트

반응식

HRID 54459 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b67afbf0e52346d9bc70416d655afc1b
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622964

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