Pyridoxamine, dihydrochloride → Menadione

HRID 1382793

Reaction equation

HRID 1382793 reaction equation
CC1C(O)=C(CN)C(CO)=CN=1.Cl.Cl.[CH3:15][C:16]1(S([O-])(=O)=O)[C:26](=[O:27])[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:18](=[O:19])[CH2:17]1.O.O.O.[Na+]>O>[CH3:15][C:16]1[C:26](=[O:27])[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:18](=[O:19])[CH:17]=1

Participants

4

Reactant 2

HCID 10664Pyridoxamine, dihydrochlorideHCID 23677974Sodium 2-methyl-1,4-dioxo-1,2,3,4-tetrahydronaphthalene-2-sulfonate--water (1/1/3)

Product 1

HCID 4055Menadione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution containing 2.0 grams of pyridoxamine dihydrochloride, purity 98%, (0.00813 moles), in 10 ml of water, at room temperature, was added dropwise during 5 minutes, to a stirred solution of 5.2 grams of menadione sodium bisulfite, purity 95%, (0.01496 moles), in 13 ml of water. After a few minutes of stirring at a temperature of 25° C., a white crystalline precipitate formed. The product was filtered, washed with a few milliliters of ice cold water, then dried in vacuum at 40°-45° C. until constant weight was achieved. The recovered dry product was a white crystalline powder weighing 5.05 grams. The assay gave a combined menadione content equal to 48.5%, with a yield (based on MSB) equal to 95% and a purity of 95.3%. The so obtained compound melted, with decomposition, at 171°-173° C. The product was moderately soluble in water (1.3 g/100 ml of water).

Workup

  1. customa white crystalline precipitate formed
  2. filtrationThe product was filtered
  3. washwashed with a few milliliters of ice cold water
  4. customdried in vacuum at 40°-45° C. until constant weight

Sources & evidence

ORD record
ord-6a9fce84b9a94e0ea22e028637e667f8
Source dataset
uspto-grants-1989_02
Patent number
US04808602

Linked notes

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