Nitric Acid → 5-Acetyl-3-nitrosalicylic acid

HRID 614831Notes

Reaction equation

HRID 614831 reaction equation
[C:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15].O>S(=O)(=O)(O)O>[C:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 831515-Acetylsalicylic acid

Product 1

HCID 130269385-Acetyl-3-nitrosalicylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Acetylsalicylic acid (9.0 g) was dissolved in concentrated sulphuric acid (20 ml). The solution was cooled to 0° C. and treated, with stirring, with a mixture of concentrated nitric acid (density 1.42; 3.8 ml) and concentrated sulphuric acid (3.8 ml), dropwise, at such a rate that the temperature did not exceed 5° C. The mixture was left to stand at 0° C. for 5 hours and then it was poured onto a mixture of ice and water (100 ml). The precipitated solid was filtered off and recrystallized from water to give 5-acetyl-3-nitrosalicylic acid (8.6 g), m.p. 192°-193° C.

Workup

  1. additiontreated
  2. customdid not exceed 5° C
  3. waitThe mixture was left
  4. filtrationThe precipitated solid was filtered off
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-7f05cda3ff0245e3802381ce70e0bdbd
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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