Hydroxylamine → Benzonitrile, 3,4-dihydroxy-5-nitro-

HRID 725296Notes

Reaction equation

HRID 725296 reaction equation
[NH2:1]O.[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=O>O>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[C:7]#[N:1]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 5748958Benzonitrile, 3,4-dihydroxy-5-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 1.7 g of hydroxylamine, O-sulfonic acid in 6 ml of water is added to a solution of 1.83 g of 3,4-dihydroxy-5-nitrobenzaldehyde in 25 ml of water, subsequently stirred at 65° for 3.5 hours, cooled, the separated precipitate is filtered off under suction and taken up in ethyl acetate. The organic phase is dried over sodium sulfate and evaporated in a water-jet vacuum. The crystals obtained are recrystallized from ethyl acetate/n-hexane. There is obtained 3,4-dihydroxy-5-nitrobenzonitrile in the form of yellow crystals of m.p. 194°-195°.

Workup

  1. temperaturecooled
  2. filtrationthe separated precipitate is filtered off under suction
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated in a water-jet vacuum
  5. customThe crystals obtained
  6. customare recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ba04f1cc727b4696bbd9e39873852eba
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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