Hydrogen Bromide → HCID 69424217, compound

HRID 1181158Notes

Reaction equation

HRID 1181158 reaction equation
C([NH:8][C:9]1[N:13]([CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[N:12]=[C:11]([Br:19])[C:10]=1[N+:20]([O-])=O)C1C=CC=CC=1.[OH-].[Na+].Br>CCO.[Pd]>[BrH:19].[NH2:20][C:10]1[CH:11]=[N:12][N:13]([CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[C:9]=1[NH2:8]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 13007231HCID 13007231, compound

Product 1

HCID 69424217HCID 69424217, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propane-1,2-diol (4-4) (7.0 g; 18.8 mmol) in EtOH (150 ml) containing 10% Pd/C as catalyst (Engelhard, 50% wet, 0.7 g dry weight) and NaOH (solid, 800 mg, 18.8 mmol) was hydrogenated in an autoclave (1 l) at 16 bar for 3.5 hours. The reaction mixture was filtered to remove the catalyst under an inert atmosphere, in an ethanolic solution containing HBr (47%, 7.1 ml, 57 mmol). The solvent was evaporated off under reduced pressure to give a solid. After washing with cold EtOH, the 3-(4,5-diaminopyrazol-1-yl)propane-1,2-diol hydrobromide was obtained as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst under an inert atmosphere
  3. customThe solvent was evaporated off under reduced pressure
  4. customto give a solid
  5. washAfter washing with cold EtOH

Sources & evidence

ORD record
ord-939e274379f84ceda48a750a1efb8192
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

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