HCID 67308922, compound → HCID 45078774, compound

HRID 1045965Notes

Reaction equation

HRID 1045965 reaction equation
[CH3:1][O:2][C:3]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]([CH3:11])[N:4]=1>CO.[Pd]>[NH3:4].[CH3:1][O:2][C:3]1[C:7]([NH2:8])=[CH:6][N:5]([CH3:11])[N:4]=1

Participants

5

Reactant 1

HCID 67308922HCID 67308922, compound

Product 2

HCID 222AmmoniaHCID 45078774HCID 45078774, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Methoxy-1-methyl-4-nitropyrazole (2.9 g) was dissolved in MeOH (100 ml) at room temperature and Pd/C (0.58 g, 50% wet) was added. The solution was purged with nitrogen for 10 minutes, followed by hydrogen for 2.5 hours. The reaction mixture was filtered through a cake of celite, washed with EtOAc (200 ml) and the volatiles removed under vacuum to give the crude product as a deep red oil. Column chromatography (SiO2; 50:50, EtOAc:heptane), followed by further purification via a ‘catch and release’ method (2 g isolute flash SCX-2, eluting with 100% MeOH then methanolic ammonia (0.5 M to 7 M) furnished 3-methoxy-1-methylpyrazol-4-amine as a deep blue liquid (0.551 g). NMR Spectrum: (CDCl3) 2.35 (m, 2H), 3.62 (s, 3H), 3.94 (s, 3H), 6.83 (s, 1H); Mass spectrum: MH+ 128.

Workup

  1. customThe solution was purged with nitrogen for 10 minutes
  2. filtrationThe reaction mixture was filtered through a cake of celite
  3. washwashed with EtOAc (200 ml)
  4. customthe volatiles removed under vacuum
  5. customto give the crude product as a deep red oil
  6. customColumn chromatography (SiO2; 50:50, EtOAc:heptane), followed by further purification via a ‘catch and release’ method (2 g isolute flash SCX-2
  7. washeluting with 100% MeOH

Sources & evidence

ORD record
ord-572211b58cba45fdb4ccaaff5b9647dd
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

Loading…