2-Methyl-5-nitrobenzofuran → 2-Methyl-5-benzofuranamine

HRID 1766286Notes

Reaction equation

HRID 1766286 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:5]=2[CH:6]=1>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[CH:6][C:5]=2[CH:7]=1

Participants

4

Reactant 1

HCID 44874532-Methyl-5-nitrobenzofuran

Product 1

HCID 31574842-Methyl-5-benzofuranamineYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-nitro-benzofuran [19] (125 mg, 0.706 mmol) in methanol (20 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm H2 for 4 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica plug to afford 5-amino-2-methyl benzofuran as a red-brown oil (78 mg, 75%), single spot at Rf 0.45 (1:1 hexane:ethyl acetate). 1H NMR (CDCl3): δ 7.17 (1H, d, J=8.7 Hz), 6.75 (1H, d, J=2.5 Hz), 6.57 (1H, dd, J8.7, 2.5 Hz), 6.20 (1H, s), 3.53 (2H, s, NH2), 2.39 (3 H, s).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-b83a64d4cb7541459bc136ed55dc81be
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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