3-(2-Methyl-5-nitrophenyl)furan → HCID 60097992, compound

HRID 2070353Notes

Reaction equation

HRID 2070353 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:15]=[CH:14][O:13][CH:12]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:15]=[CH:14][O:13][CH:12]=1

Participants

4

Reactant 1

HCID 600980813-(2-Methyl-5-nitrophenyl)furan

Product 1

HCID 60097992HCID 60097992, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-methyl-3-(3-furyl) nitrobenzene 1 (91 mg, 0.45 mmol) and Lindlar's catalyst (0.2 mmol) in methanol was placed under an H2 atmosphere and the resulting reaction was maintained overnight at rt. The reaction mixture was filtered through Celite and the remaining solids were washed with EtOAc. The combined organic portions were concentrated to provide 74 mg (0.43 mmol, 96%) of an amber residue as 2: 1H NMR (300 MHz, CD3OD) δ 7.56 (app t, J=1.1 Hz, 1H), 7.52 (dd, J=1.7, 1.9 Hz, 1 H), 6.97 (d, J=8.0 Hz, 1H), 6.75 (d, J=2.5 Hz, 1H), 6.60 (m, 2H), 2.23 (s, 3H).

Workup

  1. customthe resulting reaction
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe remaining solids were washed with EtOAc
  4. concentrationThe combined organic portions were concentrated

Sources & evidence

ORD record
ord-2bfe6928c5f447eeae602eba26b103e0
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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