Sodium Hydroxide → HCID 136100172, compound

HRID 2165968Notes

Reaction equation

HRID 2165968 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].S(O)(O)(=O)=O.[NH2:17][OH:18].S(=O)(O)[O-].[Na+].[OH-].[Na+]>O>[OH:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[C:4](=[N:17][OH:18])[NH2:5]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 137468362,3,4-TrihydroxybenzonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 136100172HCID 136100172, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedure of Example 2, 3.5 g. of 2,3,4-trihydroxybenzonitrile were reacted in 60 ml. of water with 4 g. of hydroxylamine sulfate and 2 g. of sodium bisulfite at pH=8.0 (adjusted by addition of concentrated aqueous sodium hydroxide). The reaction mixture was maintained at ambient temperature for about one hour and was then cooled. 2,3,4-Trihydroxybenzamidoxime precipitated and the precipitate was collected by filtration. The filter cake was dissolved in dilute aqueous hydrochloric acid and the resulting solution filtered through activated charcoal. Evaporation of the volatile constituents from the filtrate under reduced pressure yielded 2,3,4-trihydroxybenzamidoxime as a hydrochloride salt, melting at 207° C. with decomposition after recrystallization. from a methanol/ethyl acetate solvent mixture; yield=9%.

Workup

  1. temperaturewas then cooled
  2. custom2,3,4-Trihydroxybenzamidoxime precipitated
  3. filtrationthe precipitate was collected by filtration
  4. dissolutionThe filter cake was dissolved in dilute aqueous hydrochloric acid
  5. filtrationthe resulting solution filtered through activated charcoal
  6. customEvaporation of the volatile constituents from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-5c13db68a2754deaa8257deb9077810d
Source dataset
uspto-grants-1990_07
Patent number
US04942253

Reaction notes

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