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Lithium hydroxide, monohydrate → 1-(Isoquinolin-1-yl)-5-methyl-1H-indole-3-carboxylic acid

HRID 492182
Notes
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Reaction equation

HRID 492182 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)[CH:21]=[CH:20][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[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)[CH:9]=1)([OH:7])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68968694Methyl 1-(isoquinolin-1-yl)-5-methyl-1H-indole-3-carboxylate

Product 1

HCID 689714021-(Isoquinolin-1-yl)-5-methyl-1H-indole-3-carboxylic acidYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028Tetrahydrofuran
Solvent

Procedure

0.319 g (7.59 mmol) of lithium hydroxide monohydrate and 60 cm3 of water are added at 25° C. to 1.2 g (3.79 mmol) of 3-methoxycarbonyl-1-(isoquinol-1-yl)-5-methyl-1H-indole dissolved in 60 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 24 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 30 cm3 of water and then triturated with 11.4 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-(isoquinol-1-yl)-5-methyl-1H-indole is obtained in the form of a white solid. Mass spectrum (EI): m/e 302 (M+·), m/e 257.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. customtriturated with 11.4 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-3eacb8f5cb8541c3a9cb131f1b489cad
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531663B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes