Water → HCID 66587471, compound

HRID 1630679Notes

Reaction equation

HRID 1630679 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].Cl[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:16][C:15]1[C:10]([N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 178526745HCID 178526745, compound

Product 1

HCID 66587471HCID 66587471, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

10.0 g (88.4 mmol) of 3-nitropyrazole and 14.4 g (97.2 mmol) of 2,3-dichloropyridine were initially charged in 50 ml of dimethylformamide, 23.9 g (173 mmol) of potassium carbonate were added and the reaction mixture was stirred at 125° C. for 18 hours. After cooling, the mixture was poured into water and the precipitated solid was filtered off. Recrystallization from isopropanol/water gave 18.1 g (90% of theory) of 3-chloro-2-(3-nitro-1H-pyrazol-1-yl)pyridine (log P: 1.83; MH+: 225.1; 1H-NMR (400 MHz, CD3CN, δ, ppm): 7.15 (s, 1H), 7.56 (d, 1H), 8.15 (d, 1H), 8.23 (d, 1H), 8.53 (m, 1H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid was filtered off
  3. customRecrystallization from isopropanol/water

Sources & evidence

ORD record
ord-b7d98ad2ad1345d997fcceca3b0050b5
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

Loading…