Aniline → 3-nitro-N-phenylpyridin-2-amine

HRID 1914003Notes

Reaction equation

HRID 1914003 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 796132-Chloro-3-nitropyridineHCID 81531Diisopropylethylamine

Product 1

HCID 6117993-nitro-N-phenylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-3-nitropyridine (structure 1 as shown in Scheme 1) was dissolved in THF (10 mL/mmol) in a round bottom flask. Aniline (1.0 eq.) (structure 2 as shown in Scheme 1) and diisopropylethylamine (1.05 eq.) were added. The reaction mixture was heated to the appropriate temperature for 4 to 36 hours. After cooling to room temperature the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (20 mL/mmol) and washed with water and brine (20 mL/mmol respectively). The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product (red to brown solid) was solidified with hexane/ethyl acetate and collected by filtration. The product was carried on to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated to the appropriate temperature for 4 to 36 hours
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (20 mL/mmol)
  4. washwashed with water and brine (20 mL/mmol respectively)
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration the solvent
  8. customwas removed under reduced pressure
  9. filtrationcollected by filtration
  10. customThe product was carried on to the next step without further purification

Sources & evidence

ORD record
ord-5b31beea556a48189d1c95c1d90bf98a
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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