Aniline → 3-nitro-N-phenylpyridin-4-amine

HRID 257418Notes

Reaction equation

HRID 257418 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.CCCCCC>O1CCOCC1.C(OCC)(=O)C>[C:12]1([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8058HexaneHCID 8471TriethylamineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 6120053-nitro-N-phenylpyridin-4-amineYield 69.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-3-nitropyridine (1.50 g, 9.46 mmol) and aniline (2.0 ml, 21.9 mmol) were dissolved in 10 ml of 1,4-dioxane, and 2 ml of triethylamine was added thereto, followed by reaction at 80° to 90° C. for 2 hours. Then, the solvent was removed by distillation under reduced pressure, and 10 ml of hexane was added to the residue to wash it. The solvent was removed by decantation. The residue was further similarly treated with 10 ml of ether. The residue was purified by silica gel column chromatography [eluent: hexane:ethyl acetate=2:1 (v/v)]to obtain 1.41 g of a yellow solid (yield: 68.8%).

Workup

  1. customfollowed by reaction at 80° to 90° C. for 2 hours
  2. customThen, the solvent was removed by distillation under reduced pressure, and 10 ml of hexane
  3. additionwas added to the residue
  4. washto wash it
  5. customThe solvent was removed by decantation
  6. additionThe residue was further similarly treated with 10 ml of ether
  7. customThe residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-cc2b8301bd004cb5afc5f1553d52a2bf
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

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