Hydrochloric Acid → 1-(Isoquinolin-3-yl)-1H-indole-3-carboxylic acid

HRID 492200Notes

Reaction equation

HRID 492200 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[N:18]=[CH:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=1)=[O:7].Cl>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[N:18]=[CH:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68970562Methyl 1-(isoquinolin-3-yl)-1H-indole-3-carboxylate

Product 1

HCID 689716371-(Isoquinolin-3-yl)-1H-indole-3-carboxylic acidYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g (11.92 mmol) of lithium hydroxide monohydrate and 15 cm3 of water are added to a solution at a temperature in the region of 22° C. of 1.1 g (3.64 mmol) of 3-methoxycarbonyl-1-(isoquinol-3-yl)-1H-indole in 15 cm3 of tetrahydrofuran. After stirring at the reflux point of the solvent for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), the residue is triturated in water and the resulting suspension is filtered. The solid obtained is suspended in 20 cm3 of water adjusted to pH 7 with N hydrochloric acid. After stirring at a temperature in the region of 22° C. for 1 hour, the solid is filtered off and dried under reduced pressure (2.7 kPa) to give 0.64 g of 3-carboxy-1-(isoquinol-3-yl)-1H-indole in the form of a white solid. IR spectrum (KBr): 1661, 1629, 1593, 1540, 1464, 1217 and 748 cm−1.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customthe residue is triturated in water
  3. filtrationthe resulting suspension is filtered
  4. customThe solid obtained
  5. stirringAfter stirring at a temperature in the region of 22° C. for 1 hour
  6. filtrationthe solid is filtered off
  7. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-4454b6492e514ff2ae8735402c8e8ffb
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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