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

HRID 2209521

반응식

HRID 2209521 반응식
[C:1]([CH:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:27]([F:30])([F:29])[F:28])[OH:26])([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]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]1([C:27]([F:30])([F:28])[F:29])[OH:26])([OH:3])=[O:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 199589053-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

생성물 1

HCID 199589043-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone수율 31.6%

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-nitrophenyl)-2,3,4,6,7,8-hexahydro-5(1H)-quinolone (7.02 g) in ethanol (40 ml) and water (40 ml) was treated with lithium hydroxide monohydrate (1.44 g). The mixture was heated at 90° C. for 30 minutes, 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 the solvent stripped to yield a brown oil which was further purified by chromatography (ethyl acetate and ethyl acetate/methanol, 4:1). 3-Carboxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (2.07 g) was obtained as a white solid. NMR: 1.85 (m,2, CH2), 2.10 (m,2, CH2), 2.33-2.60 (m,3, CH2, CH), 4.21 (d,1, J=8.7, CH), 7.47 (m,2, Ar), 7.81 (s,2, OH or NH, Ar), 7.96 (m,1H, Ar); MS: m/z=400(M).

후처리

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

출처 및 근거

ORD 기록
ord-480c93e1370342d0b56c3245b2a02056
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455253

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