Sodium hydride → HCID 14368616, compound

HRID 1089450Notes

Reaction equation

HRID 1089450 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][N:5]=1.[OH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:14][C:13]=1[C:28](OCC)=[O:29]>O1CCCC1>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([NH:3][C:28]([C:13]2[N:14]=[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[C:21]([C:12]=2[OH:11])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:29])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 661742-Amino-5-chloropyridineHCID 14883410HCID 14883410, compound

Product 1

HCID 14368616HCID 14368616, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred slurry of 2.3 g of sodium hydride in 100 ml of dry tetrahydrofuran was treated with 6.1 g of 2-amino-5-chloropyridine and immersed in an ultrasonic bath for 30 minutes. The stirred slurry was then treated with a solution of 7.0 g of 4-hydroxy-1-phenyl-3-isoquinolinecarboxylic acid, ethyl ester in 70 ml of tetrahydrofuran and refluxed for 16 hours. Thereafter, the solution was cooled to room temperature and quenched with 20 ml of water. The resulting precipitate was solubilized in 500 ml of aqueous methanol and treated with carbon dioxide gas. Recrystallization of the precipitate from 500 ml of warm dimethylformamide afforded 7.5 g (84%) of N-(5-chloro-2-pyridyl)-4-hydroxy-1-phenyl-3-isoquinolinecarboxamide, m.p. 249°-251° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. customquenched with 20 ml of water
  3. additiontreated with carbon dioxide gas
  4. customRecrystallization of the precipitate from 500 ml of warm dimethylformamide

Sources & evidence

ORD record
ord-1fd81cc79f1c49c38e95d7e5204b9072
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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