Hydrochloric Acid → HCID 22034782, compound

HRID 891831Notes

Reaction equation

HRID 891831 reaction equation
C([NH:8][C:9]1[N:13]([CH2:14][CH2:15][O:16][CH3:17])[N:12]=[C:11](Br)[C:10]=1[N+:19]([O-])=O)C1C=CC=CC=1.[ClH:22]>C(O)C.[Pd]>[ClH:22].[ClH:22].[NH2:19][C:10]1[CH:11]=[N:12][N:13]([CH2:14][CH2:15][O:16][CH3:17])[C:9]=1[NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22034786HCID 22034786, compound

Product 1

HCID 22034782HCID 22034782, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-benzylamino-3-bromo-1-(2′-methoxyethyl)-4-nitropyrazole (4 g, 2.8 mmol) in ethanol (500 ml) containing a 10% Pd/C catalyst (Johnson-Mattey Type 487, dry weight 0.5 g) and 36% hydrochloric acid (0.57 g, 5.6 mmol) is hydrogenated in a Parr Autoclave (1 l) at 1 MPa for 1 hour. The catalyst is then removed by filtration and washed with ethanol, and the filtrate is evaporated under reduced pressure. A crude orange-coloured solid (2.8 g) is thus obtained, and is triturated in EtOAc (20 ml) for 1 hour. The solid is then filtered off and washed with cold EtOAc (20 ml) and then dried under vacuum to give the 4,5-diamino-1-(2′-methoxyethyl)pyrazole in the form of a beige-coloured solid (0.7 g, 27%).

Workup

  1. customThe catalyst is then removed by filtration
  2. washwashed with ethanol
  3. customthe filtrate is evaporated under reduced pressure
  4. customA crude orange-coloured solid (2.8 g) is thus obtained
  5. customis triturated in EtOAc (20 ml) for 1 hour
  6. filtrationThe solid is then filtered off
  7. washwashed with cold EtOAc (20 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2afe9a14f7fe4cf58d342f97a32d7764
Source dataset
uspto-grants-2006_02
Patent number
US07004979B2

Reaction notes

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