Lithium hydroxide, monohydrate → 1-(2-(Trifluoromethyl)quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 1869153

反応式

HRID 1869153 の反応式
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[CH:9]=1)=[O:7]>O1CCCC1.O>[C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([C:27]([F:30])([F:28])[F:29])[CH:18]=2)[CH:9]=1)([OH:7])=[O:5]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 689705923-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole

生成物 1

HCID 689729551-(2-(Trifluoromethyl)quinolin-4-yl)-1H-indole-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

0.204 g (4.9 mmol) of lithium hydroxide monohydrate and 8 cm3 of water are added to 0.6 g (1.62 mmol) of 3-methoxycarbonyl-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole dissolved in 8 cm3 of tetrahydrofuran. After stirring at reflux for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 20 cm3 of water (pH=10). The resulting aqueous solution is washed with 30 cm3 of ethyl acetate, adjusted to pH 6 with N hydrochloric acid and extracted with 50 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is triturated in 20 cm3 of isopropyl ether and filtered off, resulting in 0.3 g of 3-carboxy-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a yellow powder. Mass spectrum (EI): m/e 356 (M+•), m/e 311.

後処理

  1. temperatureat reflux for 15 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. washThe resulting aqueous solution is washed with 30 cm3 of ethyl acetate
  5. extractionextracted with 50 cm3 of ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe solid obtained
  9. customis triturated in 20 cm3 of isopropyl ether
  10. filtrationfiltered off
  11. customresulting in 0.3 g of 3-carboxy-1-(2-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a yellow powder

出典と根拠

ORDレコード
ord-d37b4a9f20ea4fc38641b5986370be79
出典データセット
uspto-grants-2009_12
特許番号
US07638521B2

関連ノート

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