Aniline → 54904-02-8

HRID 225900Notes

Reaction equation

HRID 225900 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([NH:9][C:4]2[C:5]([Br:8])=[CH:6][CH:7]=[CH:2][N:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6115Aniline2×HCID 693532,5-Dibromopyridine

Product 1

HCID 1061060754904-02-8Yield 67%

Procedure

A mixture of 2,5-dibromopyridine (10.2 g, 43 mmole) in aniline (25 mL) was stirred and heated at reflux for 3 h. The reaction was cooled to RT and most of the aniline was distilled off under vacuum. The remaining residue was taken up in ethyl acetate and the solution was washed with 1.0 N Na2CO3 then with brine, dried (Na2SO4), and concentrated under vacuum. Trituration with petroleum ether, filtration and drying under vacuum gave the title compound (7.20 g, 67%) as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J=2.4 Hz, 1 H), 7.58 (dd, 1 H), 7.31-7.39 (m, 4 H), 7.11 (m, 1 H), 6.79 (br s, 1 H); MS (ES) m/e 249.0 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. distillationwas distilled off under vacuum
  4. washthe solution was washed with 1.0 N Na2CO3
  5. dry with materialwith brine, dried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. filtrationTrituration with petroleum ether, filtration
  8. customdrying under vacuum

Sources & evidence

ORD record
ord-f2a0d2061e314ed693f58586b6d1e6ac
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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