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

HRID 2064924Notes

Reaction equation

HRID 2064924 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH2:17][OH: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]([CH:17]=[O:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 66928541[5-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol

Product 1

HCID 70192445-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde

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-(3-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol (13.80 g, 61.83 mmol) in AcCN (631.0 mL) was treated at rt with MnO2 (35.84 g, 370.98 mmol). The reaction mixture was stirred at rt for 16 h before being filtered through Celite and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound. TLC: rf (60:40 hept-EA)=0.16. LC-MS-conditions 02: tR=0.81 min. 1H NMR (400 MHz, CDCl3) δ 5.48 (s, 2H), 6.67 (d, J=3.5 Hz, 1H), 6.96 (d, J=2.5 Hz, 1H), 7.24 (d, J=3.8 Hz, 1H), 7.64 (d, J=2.5 Hz, 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 (40:60 hept-EA)

Sources & evidence

ORD record
ord-5b60b8963474459c8606d8ca86ff7276
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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