Iodoethane → Methyl 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate

HRID 573342Notes

Reaction equation

HRID 573342 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([O:11][CH3:12])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH2:13](I)[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:13]([N:6]1[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178499180HCID 178499180, compound

Product 1

HCID 54775328Methyl 1-ethyl-4-nitro-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-nitro-1H-pyrazole-3-carboxylate (5.0 g), EtI (2.8 mL) and K2CO3 (8.1 g) in acetone (50 mL) was stirred at 50° C. for 4 h. After stirring at room temperature overnight, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.2 g).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-81918841e50747d593bb1ef17f22d105
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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