Potassium Carbonate → 4-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole

HRID 1804699Notes

Reaction equation

HRID 1804699 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].[N+:16]([C:19]1[CH:20]=[N:21][NH:22][CH:23]=1)([O-:18])=[O:17]>CC(C)=O.O>[N+:16]([C:19]1[CH:20]=[N:21][N:22]([CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:23]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 674814064-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

N-(2-chloroethyl)pyrrolidine hydrochloride (752 mg, 4.42 mmol), potassium carbonate (0.534 ml, 8.84 mmol) and 4-nitro-1H-pyrazole (500 mg, 4.42 mmol) were combined in acetone (20 ml) and the reaction was stirred at reflux for 16 hours. The reaction mixture was diluted with 75 mL water and extracted with ethyl acetate (3×20 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to give the title compound. MS (ESI(+)) m/e 210.9 (M+H)+.

Workup

  1. temperatureat reflux for 16 hours
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe86f9390b31462fb10f6df2dc4b38ce
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Reaction notes

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