Mci-186 → HCID 178432456, compound

HRID 1991448Notes

Reaction equation

HRID 1991448 reaction equation
[CH3:1][C:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.[CH3:14][C:15]1[C:20]([OH:21])=[C:19]([CH:22]=O)[C:18]([CH2:24][OH:25])=[CH:17][N:16]=1.Cl>[OH-].[Na+].O>[OH:7][C:5]1[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=[C:2]([CH3:1])[C:6]=1[CH:22]1[C:19]2[C:20]([OH:21])=[C:15]([CH3:14])[N:16]=[CH:17][C:18]=2[CH2:24][O:25]1

Participants

5

Reactant 2

HCID 4021Mci-1862×HCID 6171Pyridoxal hydrochloride

Product 1

HCID 178432456HCID 178432456, compoundYield 733.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
4 °C

Procedure

To a stirring solution of 3-methyl-1-phenyl-2-pyrazolin-5-one (1.74 g) (hereinafter, referred to edaravone) in 0.1M of NaOH (100 mL) at room temperature, were added dropwise a solution of pyridoxal hydrochloride (2.44 g) in water (100 mL) with stirring and then reacted. After dropwise, the mixture was stirred for 30 minutes and the reaction was stopped when it was appeared to finish deposition of white precipitate. The mixture was cooled to 4° C. in refrigerator to deposit sufficiently the precipitate. The reaction solution was stood to cool overnight, the white precipitate was filtered off to give crude (wet) of 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol (23.7 g).

Workup

  1. customat room temperature
  2. customreacted
  3. stirringAfter dropwise, the mixture was stirred for 30 minutes
  4. temperatureto cool overnight
  5. filtrationthe white precipitate was filtered off

Sources & evidence

ORD record
ord-3c3f0a7e10714507b7147130f6b4eaf5
Source dataset
uspto-grants-2010_01
Patent number
US07645882B2

Reaction notes

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