HCID 10910661, compound → 96134-65-5

HRID 1688097Notes

Reaction equation

HRID 1688097 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-])=O)=[N:5][N:6]=1.[H][H]>CO.C(OCC)(=O)C.[Ni]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])=[N:5][N:6]=1

Participants

6

Reactant 2

HCID 10910661HCID 10910661, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1340971296134-65-5Yield 99.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-5-(2-nitro-phenyl)-[1,3,4]oxadiazole (0.73 g) and 50% Raney Ni (1 mL) in methanol (5 mL) and ethyl acetate (25 mL) was shaken under 50 psi of hydrogen for 3 hours. Filtration through celite and concentration of the filtrate provided 0.62 g of 2-methyl-5-(2-amino-phenyl)-[1,3,4]oxadiazole: 1H NMR (400 MHz, CDCl3) δ 7.71 (dd, 1H), 7.26 (dd, 1H), 6.76 (m, 2H), 5.81 (bs, 2H), 2.61 (s, 3H).

Workup

  1. filtrationFiltration through celite and concentration of the filtrate

Sources & evidence

ORD record
ord-7832dc43a7ad497aa07cae59eee196a1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…