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

HRID 1869153

반응식

HRID 1869153 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d37b4a9f20ea4fc38641b5986370be79
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638521B2

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