Hydrochloric Acid → [1-(Benzoylamino)-6-isoquinolinyl]carboxylic acid

HRID 636927Notes

Reaction equation

HRID 636927 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([NH:23][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[N:18][CH:17]=[CH:16]2)=[O:12].Cl>O.CS(C)=O>[C:24]([NH:23][C:19]1[C:20]2[C:15](=[CH:14][C:13]([C:11]([OH:6])=[O:12])=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1)(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 22665740N-(6-formyl-1-isoquinolinyl)benzamideHCID 23668197Sodium Chlorite2×HCID 23672064Monosodium phosphate

Product 1

HCID 22665699[1-(Benzoylamino)-6-isoquinolinyl]carboxylic acidYield 230.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent3×

Procedure

To a stirred solution of 400 mg sodium chlorite and 80 mg sodium dihydrogen phosphate in 2.5 mL of water and 2.5 mL of dimethylsulfoxide in a cooling bath at room temperature was added dropwise a solution of 510 mg N-(6-formyl-1-isoquinolinyl)benzamide (1f) in 2.5 mL of dimethylsulfoxide. After 16 hours at room temperature a solution of 170 mg sodium chlorite in 0.5 mL of water and 1.0 mL of dimethylsulfoxide was added and stirred at room temperature for an additional 6 hours. Then 100 mL water was added, the pH adjusted to three using 2N hydrochloric acid and the resulting suspension was kept at 5° C. for 16 hours. The precipitate was collected to afford 450 mg of the title compound.

Workup

  1. waitthe resulting suspension was kept at 5° C. for 16 hours
  2. customThe precipitate was collected

Sources & evidence

ORD record
ord-c969e9ca8577478ebc30e266cab21b1d
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

Loading…