1,4-Dioxane hydrochloride → 1-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-amine
Reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[N:6]1.Cl.O1CCOCC1>CO.O1CCOCC1>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]1Participants
5
Procedure
N,N-dimethyl-2-(4-nitro-1H-pyrazol-1-yl)ethanamine (1.19 g, 6.46 mmol)was dissolved in methanol (65 ml) and the flask was equipped with a hydrogenation stopcock apparatus. The flask was purged with N2 and 10% Pd/C (100 mg) was added. The flask was again purged with N2, then flushed with H2 and left overnight stirring under H2 (1 atm). The reaction was purged with N2 and filtered through Celite, rinsing with methanol. The filtrate was concentrated in vacuo to give a viscous oil, which was dissolved in dioxane and treated with excess 4N HCl-dioxane, whereupon a thick and somewhat gummy precipitate formed. The mixture was concentrated to dryness and dried under vacuum.
Workup
- customthe flask was equipped with a hydrogenation stopcock apparatus
- customThe flask was purged with N2 and 10% Pd/C (100 mg)
- additionwas added
- customThe flask was again purged with N2
- customflushed with H2
- customThe reaction was purged with N2
- filtrationfiltered through Celite
- washrinsing with methanol
- concentrationThe filtrate was concentrated in vacuo
- customto give a viscous oil, which
- customwhereupon a thick and somewhat gummy precipitate formed
- concentrationThe mixture was concentrated to dryness
- customdried under vacuum
Sources & evidence
- ORD record
- ord-726742334a084f9d807ff6a343f758ee
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426408B2
Reaction notes
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