Hydrochloric Acid → (4-nitro-1H-pyrazol-1-yl)acetaldehyde

HRID 624016Notes

Reaction equation

HRID 624016 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[N:6]1.Cl>C1COCC1>[N+:10]([C:8]1[CH:7]=[N:6][N:5]([CH2:4][CH:3]=[O:2])[CH:9]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 662221331-(2,2-dimethoxyethyl)-4-nitro-1H-pyrazole

Product 1

HCID 25220516(4-nitro-1H-pyrazol-1-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(2,2-dimethoxyethyl)-4-nitro-1H-pyrazole (2.65 g, 13.2 mmol) in THF (34 mL), a 2N aq. HCl-solution (60 mL, 120 mmol) was added dropwise. After stirring at 80° C. for 2 h, the reaction mixture was allowed to reach rt and freeze-dried overnight to yield 2-(4-nitro-1H-pyrazol-1-yl)acetaldehyde which was used as an yellow oil in the next step without further purification. LC-MS conditions B: tR=0.24 min, [M+H]+=no ionization.

Workup

  1. customto reach rt
  2. customfreeze-dried overnight

Sources & evidence

ORD record
ord-841af28254d842339ab24bd2f95d9793
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

Loading…