Ethanol → 2-Methyl-5-benzofuranamine oxalate

HRID 378858Notes

Reaction equation

HRID 378858 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([OH:16])C.[CH:17]([O-:19])=[O:18].[NH4+]>[Pd].C1COCC1>[C:4]([OH:3])(=[O:16])[C:17]([OH:19])=[O:18].[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 216968642-Methyl-5-benzofuranamine oxalate

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 (415 mL). This mixture was filtered and a solution of oxalic acid (25.4 g) in methanol (80 mL) was added 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. additiona solution of oxalic acid (25.4 g) in methanol (80 mL) was added dropwise
  5. customcollected
  6. washwashed with methanol/TBME
  7. customdried

Sources & evidence

ORD record
ord-08551cd065bc4b02884dc079f22ef35c
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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