Water → 2-{3-Nitroanilino}nicotinamide

HRID 257785Notes

Reaction equation

HRID 257785 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[NH:7][C:8]1[C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:3])=[O:2].[NH4+:20].[OH-].O.[Cl-].[NH4+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[NH:7][C:8]1[C:13]([C:14](=[O:15])[NH2:20])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 19781717HCID 19781717, compound

Product 1

HCID 9019132-{3-Nitroanilino}nicotinamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-(3-nitroanilino)-3-chloroformylpyridine was dissolved in tetrahydrofuran (2000 ml) and 70 ml of 30% solution of NH4OH was added dropwise with stirring to the reaction mixture. The reaction mixture was stirred at room temperature for 18 hours. Water was added to the mixture to dissolve the solid ammonium chloride that was formed. The tetrahydrofuran was removed, and the resulting aqueous slurry was filtered and washed yielding a yellow solid. The solid was washed with water and air dried yielding 64.8 g (250 mmole, 99% yield) of 2-(3-nitroanilino)-3-carbamoylpyridine (mp 240°-241° C.).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. customwas formed
  3. customThe tetrahydrofuran was removed
  4. filtrationthe resulting aqueous slurry was filtered
  5. washwashed
  6. customyielding a yellow solid
  7. washThe solid was washed with water and air
  8. customdried

Sources & evidence

ORD record
ord-4bd6a2deea71431aa59b211d8f9d0319
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

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