Hydrochloric Acid → HCID 57642348, compound

HRID 2112540Notes

Reaction equation

HRID 2112540 reaction equation
N[C:2]1[N:6]([CH2:7][CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].N([O-])=O.[Na+].[ClH:20]>O.[Cu](Cl)Cl>[Cl:20][C:2]1[N:6]([CH2:7][CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 57642393HCID 57642393, compound

Product 1

HCID 57642348HCID 57642348, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6.7 g (0.032 mole) of ethyl 5-amino-3-methyl-1-(2-propenyl)-1H-pyrazole-4-carboxylate (XV) in 30 mL of concentrated hydrochloric acid was added 8.6 g (0.064 mole) of copper (II) chloride. The mixture was cooled to 0° C. and 2.65 g (0.038 mole) of sodium nitrite was added portionwise over 20 minutes. The mixture was stirred at room temperature for 1 hour, and then at 40° C. for 2 hours. The mixture was diluted with 50 mL of water and extracted twice with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexane (1:4) to give 5.0 g of ethyl 5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole-4-carboxylate (XVI) as a light yellow oil.

Workup

  1. waitat 40° C. for 2 hours
  2. extractionextracted twice with chloroform
  3. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-135d98de732b4cc88bd233a3155c93ce
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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