Nitrogen → 5-((4-Nitro-1H-pyrazol-1-yl)methyl)-2-furancarboxaldehyde

HRID 2064916Notes

Reaction equation

HRID 2064916 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4]>C(C#N)(C)=O.O=[Mn]=O>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 66928816[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol

Product 1

HCID 36059345-((4-Nitro-1H-pyrazol-1-yl)methyl)-2-furancarboxaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol (7.0 g, 15.68 mmol) in AcCN (320.0 mL) was treated at rt with MnO2 (18.2 g, 188.18 mmol). The reaction mixture was stirred at rt overnight before being filtered through Celite and the solvent was removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound. TLC: rf (60:40 hept-EA)=0.16. LC-MS-conditions 02: tR=0.80 min. 1H NMR (400 MHz, CDCl3) δ 5.44 (s, 2H), 6.66 (d, J=3.5 Hz, 1H), 7.25 (d, J=3.5 Hz, 1H), 8.10 (s, 1H), 8.28 (s, 1H), 9.65 (s, 1H).

Workup

  1. filtrationbefore being filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (60:40 hept-EA)

Sources & evidence

ORD record
ord-c86c7c3788af4b31ba6856ccb6f7b6ab
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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