Acetic Acid → 4-((6-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-1-oxoisoquinolin-2(1H)-yl)methyl)benzoic acid

HRID 907262Notes

Reaction equation

HRID 907262 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:35])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=3)[CH:17]=[CH:16]4)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)C>CO>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:35])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=3)[CH:17]=[CH:16]4)[CH:12]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 57551782Methyl 4-((6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-oxoisoquinolin-2(1H)-yl)methyl)benzoate

Product 1

HCID 575518114-((6-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-1-oxoisoquinolin-2(1H)-yl)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of the product of step i) (1 g) in methanol (15 mL) at reflux was added sodium hydroxide solution (1N, 2.4 mL). The reaction mixture was then stirred at reflux for 90 minutes. Additional sodium hydroxide solution (1N, 0.5 mL) was added and heating continued for a further 40 minutes. Acetic acid (0.16 mL) was added and the reaction was stirred at room temperature for 17 hours.

Workup

  1. temperatureat reflux for 90 minutes
  2. temperatureheating
  3. stirringthe reaction was stirred at room temperature for 17 hours

Sources & evidence

ORD record
ord-a4cf08b6ed434ea69538fc7105f5db10
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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