Acetic Acid → 6-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

HRID 907274Notes

Reaction equation

HRID 907274 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:32])=[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][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[C:28]([O:30]C)=[O:29])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+].C(O)(=O)C.O>CO>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:32])=[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][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[C:28]([OH:30])=[O:29])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57551825HCID 57551825, compound

Product 1

HCID 575517606-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of step iv) (1.5 g) in methanol (20 mL) at reflux was added sodium hydroxide (1N, 5.23 mL) and the solution stirred at this temperature for 30 min. The reaction mixture was treated with acetic acid (0.34 mL) and water and stirred overnight at room temperature. The solid was filtered and washed with methanol:water (1:1) then water. The solid was dried under vacuum at 60° C. to yield the sub-title compound (1.25 g).

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe solid was filtered
  3. washwashed with methanol:water (1:1)
  4. customThe solid was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-41c16bf2485f4cccb24807ae1a4ed3d9
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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