Hydrochloric Acid → 3-Methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245245ノート

反応式

HRID 245245 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[C:6]([CH3:22])=[C:5]2[C:23]([OH:25])=[O:24].[CH3:26][S:27]([O-:29])=[O:28].[Na+].Cl>CS(C)=O.C(OCC)(=O)C.O.[Cu]I>[CH3:22][C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[N:8][C:9]2[C:4]([C:5]=1[C:23]([OH:25])=[O:24])=[CH:3][C:2]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:11][CH:10]=2

参加物

8

反応物 3

HCID 313Hydrochloric AcidHCID 2733271Sodium methanesulfinate2 回HCID 673839956-Bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

生成物 1

HCID 673841653-Methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid収率 45.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒2 回HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a suspension of 6-bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (10 g, 21.94 mmol) in dimethyl sulfoxide (146 mL) was added copper(I) iodide (8.36 g, 43.9 mmol) and sodium methanesulfinate (5.27 g, 43.9 mmol). The reaction mixture was alternately evacuated and purged with nitrogen three times and heated to 120° C. for 18 h. Additional copper(I) iodide (8.36 g, 43.9 mmol) and sodium methanesulfinate (5.27 g, 43.9 mmol) was added, and the mixture was stirred for an additional 22 h. The mixture was cooled to room temperature and diluted with ethyl acetate and water. The mixture was acidified to pH 2-3 with 2N HCl, filtered through Celite®, and rinsed with ethyl acetate. The organic layer was separated, washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (4.07 g, 30% yield) as an orange solid. MS (m/z) 410.0 (M+H+).

後処理

  1. customThe reaction mixture was alternately evacuated
  2. custompurged with nitrogen three times
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through Celite®
  5. washrinsed with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e252b030a9f34f89a16f0d0637e06e23
出典データセット
uspto-grants-2014_02
特許番号
US08658636B2

反応ノート

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