HCID 18444043, compound → HCID 17978864, compound

HRID 459671Notes

Reaction equation

HRID 459671 reaction equation
[ClH:1].[NH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[N:17]=O.[H][H]>C(O)C.[Pd]>[ClH:1].[ClH:1].[NH2:17][C:4]1[CH:5]=[N:6][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[C:3]=1[NH2:2]

Participants

5

Reactant 2

HCID 18444043HCID 18444043, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17978864HCID 17978864, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6.0 g (22.5 mmol) of 5-amino-1-(4-isopropylphenyl)-4-nitroso-1H-pyrazole hydrochloride from Step 2.2 in 150 mL of ethanol was hydrogenated for 6 hours on 0.6 g of Pd/C (10%) at 8 bar of hydrogen pressure. The catalyst was filtered off, and the filtrate was concentrated to a total volume of about 20 mL. After the addition of 40 mL of a 3-molar ethanolic hydrochloric acid solution and agitation in an ice bath, the product crystallized out. Suction filtration and washing with 50 mL of ethyl acetate gave 5 g (17.2 mmol, 77% of the theoretical) of 4,5-diamino-1-(4-isopropylphenyl)-1H-pyrazole dihydrochloride as a colorless product.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to a total volume of about 20 mL
  3. additionAfter the addition of 40 mL of a 3-molar ethanolic hydrochloric acid solution and agitation in an ice bath
  4. customthe product crystallized out
  5. filtrationSuction filtration
  6. washwashing with 50 mL of ethyl acetate

Sources & evidence

ORD record
ord-780588eaf066489db4858ec0449fea30
Source dataset
uspto-grants-2007_03
Patent number
US07195649B2

Reaction notes

Loading…