Hydrochloric Acid → (3-Bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetic acid

HRID 1372720

Reaction equation

HRID 1372720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([O:24]CC)=[O:23])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1)=[O:10].[OH-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58778618Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate

Product 1

HCID 17859108(3-Bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.64 g, 3.97 mmol) was dissolved in THF (40 ml). To the resulting solution was added 0.25N NaOH (24.0 ml, 5.95 mmol), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into 1N HCl (50 ml) to acidify the mixture. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetic acid (1.50 g, 98%) as a pale yellow solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-32f773e534ce42acac00bdeb04ff47cd
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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