Hydrochloric Acid → 2-[(1H-Imidazol-2-yl)methyl]aniline

HRID 1462437Notes

Reaction equation

HRID 1462437 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1)([O-])=O.Cl.[OH-].[Na+]>C(O)C.[Fe]>[NH2:1][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][C:7]1[NH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 112064782-(2-Nitrobenzyl)-imidazole

Product 1

HCID 133449032-[(1H-Imidazol-2-yl)methyl]aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent4×

Procedure

50% Aqueous ethanol (5,672 ml) and 2,890 g (14.22 moles) of 2-(2-nitrobenzyl)imidazole are charged into a 22 liter flask. The suspension is stirred under nitrogen atmosphere and 2,400 g (42.97 moles) of iron powder (100 mesh) are added all at once. The mixture is then warmed to 70° and a solution of 1.7 ml of 12N hydrochloric acid in 8.3 ml absolute ethanol are added. A vigorous exotherm results and a strong reflux occurs that persists for 1.5 hours. Then the exotherm subsides, a mixture of 290 ml of 12N HCl and 1400 ml of absolute ethanol are added over 30 minutes. Heat is applied and the mixture is refluxed for 2 hours, diluted with 6,500 ml of absolute ethanol and adjusted to pH 8-9 with 700 ml of 10N sodium hydroxide. The suspension is stirred for 1 hour and filtered. The cake is washed with 1,000 ml of absolute ethanol, the filtrates are combined and the solvent is removed. The remaining solid is then suspended in 10,000 ml of water, stirred under nitrogen atmosphere for two hours, collected, washed with 2,000 ml of water, and dried to yield 2-(2-aminobenzyl)imidazole, m.p. 153°-155°.

Workup

  1. temperatureThe mixture is then warmed to 70°
  2. customA vigorous exotherm results
  3. temperaturea strong reflux
  4. additionare added over 30 minutes
  5. temperatureHeat
  6. temperaturethe mixture is refluxed for 2 hours
  7. stirringThe suspension is stirred for 1 hour
  8. filtrationfiltered
  9. washThe cake is washed with 1,000 ml of absolute ethanol
  10. customthe solvent is removed
  11. stirringstirred under nitrogen atmosphere for two hours
  12. customcollected
  13. washwashed with 2,000 ml of water
  14. customdried

Sources & evidence

ORD record
ord-4c229ecf1938416fbc13411493c7946b
Source dataset
uspto-grants-1984_07
Patent number
US04460587

Reaction notes

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