5-Azidomethyl-2-carboxyethylfuran → 5-Aminomethyl-2-carboxyethylfuran

HRID 375636

Reaction equation

HRID 375636 reaction equation
[N:1]([CH2:4][C:5]1[O:9][C:8]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)=[N+]=[N-]>C(O)C.[Ni]>[NH2:1][CH2:4][C:5]1[O:9][C:8]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 189933065-Azidomethyl-2-carboxyethylfuran

Product 1

HCID 189931745-Aminomethyl-2-carboxyethylfuranYield 98.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Treatment of a solution in ethanol (50 mL) at ambient temperature of 5-azidomethyl-2-carboxyethylfuran (585 mg, 3.00 mmol), prepared as in step 3, with Raney nickel 2800 and 4 atmospheres of H2 for 24 hours, followed by filtration of the reaction mixture and concentration in vacuo gave 5-aminomethyl-2-carboxyethylfuran (0.50 g) as a yellow oil.

Workup

  1. filtrationfollowed by filtration of the reaction mixture and concentration in vacuo

Sources & evidence

ORD record
ord-6f66f430e4d846f59b020b67e134241f
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Linked notes

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