Nitric Acid → Benzamide

HRID 614814Notes

Reaction equation

HRID 614814 reaction equation
C([C:4]1[C:5](O)=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([NH:9]C1NN=NN=1)=[O:8])(=O)C.[N+]([O-])(O)=O.O>S(=O)(=O)(O)O>[C:7]([NH2:9])(=[O:8])[C:6]1[CH:15]=[CH:16][CH:17]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 178466547HCID 178466547, compound

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

3-Acetyl-2-hydroxy-N-(tetrazol-5-yl)benzamide (6.0 g) was dissolved in concentrated sulphuric acid (30 ml). The solution was then cooled to 0° C. and, with stirring, was treated with concentrated nitric acid (density 1.42; 1.62 ml) at such a rate that the temperature did not exceed 10° C. The mixture was left to stand at between 0° and 5° C. for 20 hours, and was then poured into a mixture of ice and water (300 ml). The precipitated solid was collected, washed with water, and recrystallized from 98% w/w formic acid to give 3-acetyl-2-hydroxy-5-nitro-N-tetrazol-5-yl)benzamide, m.p. 255° C. (with decomposition).

Workup

  1. customdid not exceed 10° C
  2. waitThe mixture was left
  3. customThe precipitated solid was collected
  4. washwashed with water
  5. customrecrystallized from 98% w/w formic acid

Sources & evidence

ORD record
ord-e3c9e0a871ed4f30bbe4b437d2831252
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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