Aniline → 2-Bromo-5-nitro-N-phenyl-4-pyridineamine

HRID 1986365Notes

Reaction equation

HRID 1986365 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 160998502,4-Dibromo-5-nitropyridine

Product 1

HCID 860451242-Bromo-5-nitro-N-phenyl-4-pyridineamineYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Step 2 (7.55 g, 26.8 mmol) in THF (80 mL) and triethylamine (3.7 mL, 26.8 mmol) was treated with aniline (2.6 g, 27.9 mmol) and allowed to stir at rt until the reaction was judged complete by TLC. The solvent was removed in vacuo and the residue dissolved in ethyl acetate, washed (3×) with water and brinde, dried over Na2SO4 and concentrated in vacuo to afford the title compound (7.65 g, 97%). MS (ES+) m/e 294/296 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed (3×) with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ab71254b65040bf9a31100e3ecc3e36
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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