Potassium Hydroxide → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

HRID 472160

Reaction equation

HRID 472160 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:6]=1.O.O.Cl[Sn]Cl.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 61436Stannous chloride dihydrateHCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazole

Product 1

HCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamineYield 10,152.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-methyl-1H-imidazol-1-yl)nitrobenzene (22.5 g; 0.87 mmol) is dissolved in abs. ethanol (250 mL), then SnCl2.2H2O (125 g; 0.55 mol) is added portion-wise, on cooling at 0° C. The resulting mixture is stirred at r.t. for 2 hours and heated at reflux overnight. The reaction mixture is then cooled at r.t. and the pH is adjusted to 12, by adding 30% KOH (500 mL), then KOH pellets under stirring. The resulting suspension is filtered and the cake is washed with ethanol, the combined filtrate and washings are concentrated and the residue is extracted with DCM. Concentration of the combined organic extracts afforded the title product as a slight brown solid (15.3 g; 80%), m.p.: 122-125° C. C10H11N3, MW 173.22.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture is then cooled at r.t.
  4. filtrationThe resulting suspension is filtered
  5. washthe cake is washed with ethanol
  6. concentrationthe combined filtrate and washings are concentrated
  7. extractionthe residue is extracted with DCM

Sources & evidence

ORD record
ord-38007aa131cc43e6ac40724e0553f5da
Source dataset
uspto-grants-2014_01
Patent number
US08633208B2

Linked notes

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