Nitric Acid → 3-Nitro-5-(pyrid-3-ylmethyl)-2-pyridone

HRID 34914Notes

Reaction equation

HRID 34914 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)[CH:2]=1.S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21].[OH-].[NH4+]>>[N+:20]([C:10]1[C:11](=[O:14])[NH:12][CH:13]=[C:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:9]=1)([O-:22])=[O:21]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 19851772HCID 19851772, compound

Product 1

HCID 198517853-Nitro-5-(pyrid-3-ylmethyl)-2-pyridone

Procedure

5-(Pyrid-3-ylmethyl)-2-pyridone (10 g) was added to concentrated sulphuric acid (20 ml) with cooling and stirring. Fuming nitric acid (4.5 ml) was then added over 10 mins. with cooling (ice-bath), allowed to warm to room temperature overnight and then poured on to ice (200 ml). Concentrated ammonium hydroxide solution was added to bring the pH to 8, when the product precipitated from solution. The solid was filtered off and recrystallised from methanol to give the title compound (7.04 g), m.p. 216°-7° C.

Workup

  1. temperaturewith cooling
  2. temperaturewith cooling (ice-bath)
  3. customprecipitated from solution
  4. filtrationThe solid was filtered off
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-0ca7cf7645cb4e8ca425a3c99d2d7011
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Reaction notes

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