Methylamine → Methyl[(1-methyl-3-nitro-1H-pyrazol-5-YL)methyl]amine

HRID 1919115Notes

Reaction equation

HRID 1919115 reaction equation
[CH3:1][NH2:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1>CC(C)=O>[CH3:1][NH:2][CH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 585403565-(Bromomethyl)-1-methyl-3-nitro-1H-pyrazole

Product 1

HCID 58044304Methyl[(1-methyl-3-nitro-1H-pyrazol-5-YL)methyl]amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of MeNH2 (30% wt in H2O) (2.5 g, 20 mmol) in acetone (10 mL) at 0° C. (ice bath) was added K2CO3 (415 mg, 3 mmol), followed by the dropwise addition of a solution of 5-(bromomethyl)-1-methyl-3-nitro-1H-pyrazole (220 mg, 1 mmol) in acetone (5 mL). The reaction mixture was then warmed to room temperature and stirred for 3 h. The solvent was removed and the residue was extracted with methylene chloride (15 mL×3), dried over Na2SO4 and concentrated to afford 320a as a yellow oil (170 mg, 99%), which was used in the next step without additional purification. LCMS: (M+H)+ 171

Workup

  1. customThe solvent was removed
  2. extractionthe residue was extracted with methylene chloride (15 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8eab48486fa14c70a7d8218312022b6c
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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