Citric Acid → 5-(3-Aminoisoquinolin-7-yl)-6-methylnicotinic acid

HRID 468920Notes

Reaction equation

HRID 468920 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[C:13]([CH3:22])=[N:14][CH:15]=[C:16]([CH:21]=1)[C:17]([O:19]C)=[O:18])[CH:6]=2.O1CCCC1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[C:13]([CH3:22])=[N:14][CH:15]=[C:16]([CH:21]=1)[C:17]([OH:19])=[O:18])[CH:6]=2

Participants

5

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67975074Methyl 5-(3-aminoisoquinolin-7-yl)-6-methylnicotinate

Product 1

HCID 679750675-(3-Aminoisoquinolin-7-yl)-6-methylnicotinic acidYield 63.7%

Procedure

To a mixture of methyl 5-(3-aminoisoquinolin-7-yl)-6-methylnicotinate (189 mg; 0.6444 mmol) and tetrahydrofuran (4.0 mL; 49 mmol) was added lithium hydroxide (2.0 mL; 2.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified with 10% aqueous citric acid (2 mL), and the resulting yellow precipitate recovered via filtration, washed with water and tetrahydrofuran, and dried under vacuum to yield 114.6 mg of the title compound, which was carried forward without purification. LCMS (ESI): M+H=280.1.

Workup

  1. filtrationthe resulting yellow precipitate recovered via filtration
  2. washwashed with water and tetrahydrofuran
  3. customdried under vacuum

Sources & evidence

ORD record
ord-95f853849fb94663a50de9ac8e03ad90
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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