Sulfuric Acid → 3,4-Dihydroxy-5-nitrobenzamide

HRID 2260289Notes

Reaction equation

HRID 2260289 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[C:5]#[N:6].S(=O)(=O)(O)[OH:15]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[C:5]([NH2:6])=[O:15]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 5748958Benzonitrile, 3,4-dihydroxy-5-nitro-

Product 1

HCID 214591543,4-Dihydroxy-5-nitrobenzamide

Procedure

A total of 7.2 g of 3,4-dihydroxy-5-nitrobenzonitrile are introduced portionwise into 130 ml of conc. sulfuric acid while stirring within 10 minutes, whereupon the mixture is stirred at 50° for 4 hours. The reaction mixture is poured into 800 ml of ice-water. The separated precipitate is filtered under suction, washed with water and taken up in ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. After recrystallization from acetone/ethyl acetate there is obtained 3,4-dihydroxy-5-nitrobenzamide in the form of orange crystals of m.p. 235°-236°.

Workup

  1. stirringis stirred at 50° for 4 hours
  2. filtrationThe separated precipitate is filtered under suction
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customAfter recrystallization from acetone/ethyl acetate there

Sources & evidence

ORD record
ord-6fd0a29b0d034c7196432aa8ba8af5a7
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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