HCID 17978859, compound → HCID 17978866, compound

HRID 459669Notes

Reaction equation

HRID 459669 reaction equation
[ClH:1].[NH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[N:16]=O.[H][H]>C(O)C.[Pd]>[ClH:1].[ClH:1].[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[C:3]([NH2:2])=[C:4]([NH2:16])[CH:5]=[N:6]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 17978859HCID 17978859, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17978866HCID 17978866, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.0 g (31 mmol) of 5-amino-1-(4-methoxyphenyl)4-nitrosopyrazole hydrochloride from Step 1.2 in 200 mL of ethanol was hydrogenated for 6 hours on 0.8 g of Pd/C (10%) at 8 bar of hydrogen pressure. The catalyst was filtered off, and the reaction mixture was concentrated to a total volume of about 30 mL. After the addition of 40 mL of 3-molar ethanolic hydrochloric acid and agitation in an ice bath, the product crystallized. Suction filtration and washing with 50 mL of ethyl acetate gave 7.4 g (27 mmol), 86% of the theoretical) of 1-(4-methoxyphenyl)-4,5-diamino-1H-pyrazole dihydrochloride.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe reaction mixture was concentrated to a total volume of about 30 mL
  3. additionAfter the addition of 40 mL of 3-molar ethanolic hydrochloric acid and agitation in an ice bath
  4. customthe product crystallized
  5. filtrationSuction filtration
  6. washwashing with 50 mL of ethyl acetate

Sources & evidence

ORD record
ord-db98e834436944769038605815ac00ae
Source dataset
uspto-grants-2007_03
Patent number
US07195649B2

Reaction notes

Loading…