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

HRID 54439

反応式

HRID 54439 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

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-nitrophenyl)-2,3,4,6,7,8-hexahydro-5(1H)-quinolone (7.02 g) in ethanol (40ml) and water (40ml) 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).

後処理

  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)

出典と根拠

ORDレコード
ord-e44ffa27fb374f98bef38cc0ef1eb098
出典データセット
uspto-grants-1997_04
特許番号
US05622964

関連ノート

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