4-Azidomethyl 1-(4-iodophenyl)imidazole → 4-Aminomethyl 1-(4-iodophenyl)imidazole

HRID 642997Notes

Reaction equation

HRID 642997 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:9]=1)=[N+]=[N-]>CO.[Ni]>[I:16][C:13]1[CH:12]=[CH:11][C:10]([N:8]2[CH:9]=[C:5]([CH2:4][NH2:1])[N:6]=[CH:7]2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 592600984-Azidomethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 592601094-Aminomethyl 1-(4-iodophenyl)imidazoleYield 90.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(azidomethyl)-1-(4-iodophenyl)-1H-imidazole 9.6 (0.725 g, 2.23 mmol) over Ra—Ni (50% aq. slurry, 300 mg) in MeOH (12 mL) was hydrogenated under balloon H2 for 3 h. The mixture was filtrated through CELITE. The filtrate was concentrated in vacuo to give (1-(4-iodophenyl)-1H-imidazol-4-yl)methanamine 9.7 as a solid (0.603 g). MS 300.0 (M+H).

Workup

  1. filtrationThe mixture was filtrated through CELITE
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cd8af94c38eb4ceba1ce0b0ba7adb808
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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