Lithium hydroxide, monohydrate → 5-Methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

HRID 492188Notes

Reaction equation

HRID 492188 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=2)[N:10]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH:9]=1)=[O:7]>O1CCCC1.O>[C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=2)[N:10]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68968705Methyl 5-methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylate

Product 1

HCID 689687005-Methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.422 g (10.05 mmol) of lithium hydroxide monohydrate and 50 cm3 of water are added at 25° C. to 1.06 g (3.35 mmol) of 3-methoxycarbonyl-5-methyl-1-(quinol-4-yl)-1H-indole dissolved in 50 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 22 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 25 cm3 of water and then triturated with 10 cm3 of N hydrochloric acid. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 0.996 g of 3-carboxy-5-methyl-1-(quinol-4-yl)-1H-indole is obtained in the form of a white solid. Mass spectrum (EI): m/e 302 (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 10 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-8d9ac5f61d3649a99f3a0a68cad32a33
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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