2-Aminopyridine → HCID 14368613, compound

HRID 1089449Notes

Reaction equation

HRID 1089449 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[OH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:13][C:12]=1[C:27](OCC)=[O:28]>C1C=CC=CC=1>[OH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:13][C:12]=1[C:27]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:28]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 14883410HCID 14883410, compound

Product 1

HCID 14368613HCID 14368613, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred slurry of 1.14 g of sodium hydride (as a 50% oil dispersion) in 100 ml of benzene was added 2.25 g of 2-aminopyridine. After stirring at room temperature for 15 minutes the slurry was treated with a solution of 2.25 g of 4-hydroxy-1-phenyl-3-isoquinolinecarboxylic acid, ethyl ester in 50 ml of benzene. After refluxing for one hour, the reaction mixture was cooled to room temperature, quenched with water, and extracted with three 100 ml aliquots of hot tetrahydrofuran. The organic layer was dried over magnesium sulfate, filtered, and evaporated to yield 1.7 g (65%) of 4-hydroxy-1-phenyl-N-(2-pyridyl)-3-isoquinolinecarboxamide. Recrystallization from dichloromethane afforded the analytical sample, m.p. 228°-230° C.

Workup

  1. temperatureAfter refluxing for one hour
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with three 100 ml aliquots of hot tetrahydrofuran
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9adba1608db940079b4dba949623167f
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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