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

HRID 492195Notes

Reaction equation

HRID 492195 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]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]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]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68969653Methyl 1-(quinolin-6-yl)-1H-indole-3-carboxylate

Product 1

HCID 689685141-(Quinolin-6-yl)-1H-indole-3-carboxylic acidYield 106.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.283 g (6.75 mmol) of lithium hydroxide monohydrate and 30 cm3 of water are added at 22° C. to 0.68 g (2.25 mmol) of 3-methoxycarbonyl-1-(quinol-6-yl)-1H-indole dissolved in 30 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 31.5 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 6 cm3 of N hydrochloric acid. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 0.69 g of 3-carboxy-1-(quinol-6-yl)-1H-indole is obtained in the form of a beige-coloured solid. Mass spectrum (DCI): m/e 289 (M+H)+, m/e 245.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. customtriturated with 6 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-479b5e747dbb4d8095c3b50fabfd0c50
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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