Hydrochloric Acid → HCID 19610455, compound

HRID 1857991Notes

Reaction equation

HRID 1857991 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O.[ClH:16]>[Pd].C(O)C>[ClH:16].[ClH:16].[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 1231551-(4-Nitrophenyl)-1H-imidazole

Product 1

HCID 19610455HCID 19610455, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(imidazol-1-yl)nitrobenzene (89.60 g, 0.474 mol) and 10% palladium on carbon (4.50 g) in ethanol (1200 ml) and 5N HCl (189 ml) was hydrogenated in two batches at 40 psi for 80 minutes. Water (450 ml) was then added to dissolve the product and the catalyst was removed by filtration, washing with more water, and the combined filtrates were evaporated in vacuo, using finally a freeze drier, to give 105.4 g (96%) of the title compound as a cream solid. δH (250 MHz, D2O) 7.22 (2H, d, J=8.8 Hz), 7.35 (1H, t, J=2.1 Hz), 7.44 (2H, d, J=9.0 Hz), 7.59 (1H, t, J=1.8 Hz), 8.89 (1H, t, J=1.5 Hz).

Workup

  1. dissolutionto dissolve the product
  2. customthe catalyst was removed by filtration
  3. washwashing with more water
  4. customthe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-ebcf7e05c7d44db785420b5dfd00709f
Source dataset
uspto-grants-2000_11
Patent number
US06150391

Reaction notes

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