Nitrogen → 5-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde

HRID 2064926Notes

Reaction equation

HRID 2064926 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH:17]([OH:19])[CH3:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4]>C(C#N)(C)=O.O=[Mn]=O>[N+:3]([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4].[N+:3]([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH:17]=[O:19])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 2

HCID 947NitrogenHCID 669290231-[5-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol

Product 2

HCID 70192445-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehydeHCID 669284331-[5-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanone

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 1-[5-(3-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol (6.50 g, 27.40 mmol) in AcCN (269.0 mL) was treated at rt with MnO2 (15.881 g, 164.40 mmol) and the reaction mixture was stirred at rt for 16 h before being filtered through Celite. The solvent was removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a mixture with 5-(3-nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde. TLC: rf (50:50 hept-EA)=0.20. LC-MS-conditions 02: tR=0.83 min. 1H NMR (400 MHz, CDCl3) characteristic signals δ 2.47 (s, 3H), 5.46 (s, 2H), 6.61 (d, J=3.5 Hz, 1H), 6.95 (d, J=2.3 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H).

Workup

  1. filtrationbefore being filtered through Celite
  2. customThe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (50:50 hept-EA)

Sources & evidence

ORD record
ord-5875d668dd3d498f817efdbaa310b13f
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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