Hydrochloric Acid → 3-(4-nitro-1H-pyrazol-1-yl)propanal
Reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[N:7]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[N+:11]([C:9]1[CH:8]=[N:7][N:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:10]=1)([O-:13])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-(3,3-dimethoxypropyl)-4-nitro-1H-pyrazole (1.00 g, 4.65 mmol) in THF (20 mL), a 2N aq. HCl-solution (22 mL, 44 mmol) was added dropwise. After stirring at 80° C. for 10 min, the reaction mixture was allowed to reach rt, then sat. aq. NaHCO3-solution was added to the reaction mixture and the solvent was removed under reduced pressure. The remaining aq. layer was extracted with EtOAc (2×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 3-(4-nitro-1H-pyrazol-1-yl)propanal as yellow oil which was used in the next step without further purification. LC-MS conditions B: tR=0.33 min, [M+H]+=no ionization.
Workup
- customto reach rt
- customthe solvent was removed under reduced pressure
- extractionThe remaining aq. layer was extracted with EtOAc (2×)
- dry with materiallayers were dried (MgSO4)
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-fb6583ff68f147599045d7b485550823
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303023B2
Reaction notes
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