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

HRID 1502437Notes

Reaction equation

HRID 1502437 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-8a5f53c4fa8e415881e2c3448cabedd2
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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