Ammonium Hydroxide → HCID 21405299, compound

HRID 972754Notes

Reaction equation

HRID 972754 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].[NH4+:14].[OH-]>S(Cl)(Cl)=O>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH2:14])=[O:6]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21405273HCID 21405273, compound

Product 1

HCID 21405299HCID 21405299, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 0.5 g 2-methyl-3-nitroisonicotinic acid and 20 ml of thionyl chloride was refluxed gently for 30 min. and the excess thionyl chloride was removed in vacuo to leave an oil, which was treated with conc. NH4OH under cooling for 20 min. and extracted with EtOAc. The extract was washed with water and dried, the solvent was removed to give an oil, which was purified over silica gel to yield 0.2 g of 2-methyl-3-nitroisonicotinamide, mp 203° - 204° C.

Workup

  1. temperaturewas refluxed gently for 30 min.
  2. customthe excess thionyl chloride was removed in vacuo
  3. customto leave an oil, which
  4. temperatureunder cooling for 20 min.
  5. extractionextracted with EtOAc
  6. washThe extract was washed with water
  7. customdried
  8. customthe solvent was removed
  9. customto give an oil, which
  10. customwas purified over silica gel

Sources & evidence

ORD record
ord-cb067b8a43f44558a9068c45a96a91b2
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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