Methanol → 1-Allyl-5-chloro-3-methyl-1H-pyrazol-4-amine

HRID 2112543Notes

Reaction equation

HRID 2112543 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[C:3]=1[N+:11]([O-])=O.[Cl-].[NH4+].CO>[Zn].O>[NH2:11][C:3]1[C:4]([CH3:10])=[N:5][N:6]([CH2:7][CH:8]=[CH2:9])[C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 57642378HCID 57642378, compound

Product 1

HCID 576423441-Allyl-5-chloro-3-methyl-1H-pyrazol-4-amineYield 23.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.5 g (0.00248 mole) of 5-chloro-3-methyl-4-nitro-1-(2-propenyl)-1H-pyrazole (XX), 1.6 g (0.0198 mole) of ammonium chloride, 1.6 g of zinc powder, 20 mL of methanol and 20 mL of water was stirred at room temperature for 1 hour. The mixture was filtered, and the filtrate extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with ethyl acetate-hexane (1:1) gave 0.10 g of 4-amino-5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole (XIII), which was identical to the material prepared in Example 88 (method 1) above.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by silica gel chromatography
  7. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-eea9b8c1f690496ca979385a25ae85fa
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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