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

HRID 1607032Notes

Reaction equation

HRID 1607032 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-6fd35520f34c4277a9fe8a620467729c
Source dataset
uspto-grants-1989_09
Patent number
US04863933

Reaction notes

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