2-Chloro-3-nitropyridine → N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine

HRID 2272702Notes

Reaction equation

HRID 2272702 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:4][C:3]=1[F:9]

Participants

3

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 27365114-Chloro-3-fluoroaniline

Product 1

HCID 86730067N-(4-chloro-3-fluorophenyl)-3-nitropyridin-2-amine

Conditions

Temperature
180 °C

Procedure

4-Chloro-3-fluoroaniline (10.0 g, 68.7 mmol) was heated to 180° C. in an oil bath. 2-Chloro-3-nitropyridine (11.0 g, 69.4 mmol) was added, and the resulting mixture was stirred at 180° C. for 10 minutes. The reaction mixture was then cooled to 15° C. and washed with petroleum ether, providing the product as a salmon-pink solid. Yield: 15 g, 56 mmol, 82%. 1H NMR (400 MHz, CDCl3) δ 10.20 (br s, 1H), 8.57 (dd, J=8.3, 1.6 Hz, 1H), 8.54 (dd, J=4.6, 1.7 Hz, 1H), 7.90 (dd, J=11.3, 2.4 Hz, 1H), 7.38 (dd, J=8.5, 8.3 Hz, 1H), 7.23-7.28 (m, 1H, assumed; partially obscured by solvent peak), 6.94 (dd, J=8.3, 4.5 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was then cooled to 15° C.
  2. washwashed with petroleum ether

Sources & evidence

ORD record
ord-b8b1264e1500416288db7f020a2b46d0
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

Loading…