Lithium hydroxide, monohydrate → 1-(Quinolin-3-yl)-1H-indole-3-carboxylic acid

HRID 492191Notes

Reaction equation

HRID 492191 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[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[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[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68972286Methyl 1-(quinolin-3-yl)-1H-indole-3-carboxylate

Product 1

HCID 689698981-(Quinolin-3-yl)-1H-indole-3-carboxylic acidYield 150.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.291 g (6.93 mmol) of lithium hydroxide monohydrate and 30 cm3 of water are added at a temperature in the region of 22° C. to 0.7 g (2.31 mmol) of 3-methoxycarbonyl-1-(quinol-3-yl)-1H-indole dissolved in 30 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 18 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 15 cm3 of water and then triturated with 7 cm3 of N hydrochloric acid. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 1 g of 3-carboxy-1-(quinol-3-yl)-1H-indole is obtained in the form of a pale yellow solid. Mass spectrum (EI): m/e 288 (M+·).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. customtriturated with 7 cm3 of N hydrochloric acid
  4. filtrationAfter filtering off
  5. customdrying the solid residue under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-fc20667c57d74f44b1c616a276ea720f
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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