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

HRID 492179Notes

Reaction equation

HRID 492179 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:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N: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[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68972887Methyl 1-(quinolin-2-yl)-1H-indole-3-carboxylate

Product 1

HCID 689704111-(Quinolin-2-yl)-1H-indole-3-carboxylic acidYield 111.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.390 g (9.3 mmol) of lithium hydroxide monohydrate and 45 cm3 of water are added at 25° C. to 0.935 g (3.1 mmol) of 3-methoxycarbonyl-1-(quinol-2-yl)-1H-indole dissolved in 45 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 20 cm3 of water and then triturated with 9.3 cm3 of N hydrochloric acid. After filtering off and drying under reduced pressure (2.7 kPa) at 40° C., 1 g of 3-carboxy-1-(quinol-2-yl)-1H-indole is obtained in the form of a white solid. Mass spectrum (DCI): m/e 289 (M+H)+.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. customtriturated with 9.3 cm3 of N hydrochloric acid
  4. filtrationAfter filtering off
  5. customdrying under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-2212633022e4463293e75124b244e1f4
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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