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Lithium hydroxide, monohydrate → 1-(6-(Trifluoromethyl)quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 1869157
Notes
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Reaction equation

HRID 1869157 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]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=3)[N:20]=[CH:19][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]=[C:24]([C:27]([F:30])([F:28])[F:29])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)([OH:7])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 689686183-methoxycarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole

Product 1

HCID 689691541-(6-(Trifluoromethyl)quinolin-4-yl)-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.32 g (7.63 mmol) of lithium hydroxide monohydrate and 8 cm3 of water are added to 0.94 g (2.54 mmol) of 3-methoxycarbonyl-1-(6-(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 0.73 g of 3-carboxy-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a white powder. Mass spectrum: m/e 356 (M+•).

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 0.73 g of 3-carboxy-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole in the form of a white powder

Sources & evidence

ORD record
ord-cb6c9dbd94974e77bf0cbf67feaa78d8
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07638521B2

Reaction notes

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