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

HRID 1869153

Reaction equation

HRID 1869153 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d37b4a9f20ea4fc38641b5986370be79
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Linked notes

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