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

HRID 492173Notes

Reaction equation

HRID 492173 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[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][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[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)[CH:9]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68970828Methyl 1-(isoquinolin-1-yl)-1H-indole-3-carboxylate

Product 1

HCID 689705511-(Isoquinolin-1-yl)-1H-indole-3-carboxylic acidYield 104.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.333 g (7.94 mmol) of lithium hydroxide monohydrate and 60 cm3 of water are added at 25° C. to 1.2 g (3.97 mmol) of 3-methoxycarbonyl-1-(isoquinol-1-yl)-1H-indole dissolved in 60 cm3 of tetrahydrofuran. After stirring at reflux 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 30 cm3 of water and then triturated with 8 cm3 of 5N hydrochloric acid. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 1.2 g of 3-carboxy-1-(isoquinol-1-yl)-1H-indole are obtained in the form of a white solid. Mass spectrum (EI): m/e 288 (M+·), m/e 243.

Workup

  1. temperatureat reflux for 22 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 cm3 of 5N 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-e133bf73be0b464fa492bd0e49bd5a1a
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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