2-Chloroaniline → HCID 21233940, compound

HRID 1890294Notes

Reaction equation

HRID 1890294 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([Cl:19])[N:11]=1>C(O)C>[Cl:19][C:12]1[N:11]=[C:10]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[Cl:1])[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 21233940HCID 21233940, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

2-Chloroaniline (1.32 mL, 10.4 mmol) was added to 2,6-dichloro-3-nitropyridine (1.00 g, 5.18 mmol) in ethanol (4 mL) and the solution was heated to 180° C. for 12 minutes under microwave irradiation in a heavy walled sealed tube. After cooling to room temperature, the resulting precipitate was collected by vacuum filtration, washed with cold ethanol and dried to give the title compound (0.8650 g). LCMS m/z=284.1 [M+H]+; 1H NMR (400 MHz, acetonitrile-d3) δ ppm 6.97 (d, J=8.6 Hz, 1H), 7.23 (td, J1=7.8 Hz, J2=1.6 Hz, 1H), 7.41 (td, J1=8.0 Hz, J2=1.5 Hz, 1H), 7.55 (dd, J1=8.0 Hz, J2=1.5 Hz, 1H), 8.20 (dd, J1=8.2 Hz, J2=1.50 Hz, 1H), 8.54 (d, J=8.6 Hz, 1H), 10.36 (broad s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was collected by vacuum filtration
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-0c986c0168904eb382cb66017630fcfa
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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