Lithium hydroxide, monohydrate → 5-Methyl-1-(quinolin-2-yl)-1H-indole-3-carboxylic acid

HRID 492185Notes

Reaction equation

HRID 492185 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[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N: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[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68968661Methyl 5-methyl-1-(quinolin-2-yl)-1H-indole-3-carboxylate

Product 1

HCID 689687275-Methyl-1-(quinolin-2-yl)-1H-indole-3-carboxylic acidYield 116.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.342 g (8.15 mmol) of lithium hydroxide monohydrate and 45 cm3 of water are added at 25° C. to 0.86 g (2.7 mmol) of 3-methoxycarbonyl-5-methyl-1-(quinol-2-yl)-1H-indole dissolved in 45 cm3 of tetrahydrofuran. After stirring at reflux for 19 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 8.2 cm3 of N hydrochloric acid. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 0.95 g of 3-carboxy-5-methyl-1-(quinol-2-yl)-1H-indole is obtained in the form of a white solid. Mass spectrum (EI): m/e 302 (M+·).

Workup

  1. temperatureat reflux for 19 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. customtriturated with 8.2 cm3 of N hydrochloric acid
  5. filtrationAfter filtering off
  6. customdrying the solid residue under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-ca5e36be971d467ab212c8eb95956c26
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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