Ethanol → 2-Methyl-5-benzofuranamine

HRID 378853Notes

Reaction equation

HRID 378853 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.C(O)C.C([O-])=O.[NH4+]>[Pd].C1COCC1>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 44874532-Methyl-5-nitrobenzofuran

Product 1

HCID 31574842-Methyl-5-benzofuranamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 35° C. mixture of 50 g of 2-methyl-5-nitrobenzofuran, ethanol (250 mL), THF (250 mL) and wet 10% Pd/C (4 g) was added ammonium formate (53.4 g, 0.85 mol) over 50 min. After an additional 4 h, the reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was taken up in methyl t-butyl ether. This mixture was filtered, concentrated and dried to provide 2-methyl-5-benzofuranamine which was converted to its hydrochloride salt or its oxalate salt. The oxalate was prepared as follows: To a solution of 2-methyl-5-benzofuranamine in TBME (415 mL) was added a solution of oxalic acid (25.4 g) in methanol (80 mL) dropwise. The precipitate was stirred for 2 h, collected, washed with methanol/TBME and dried to provide 2-methyl-5-benzofuranamine oxalate.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. filtrationThis mixture was filtered
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-4ffb5ed6f703406281c914226a9a8566
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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