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

HRID 1462325Notes

Reaction equation

HRID 1462325 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 were charged into a 22 liter flask. The suspension was stirred under nitrogen atmosphere and 2,400 g (42.97 moles) of iron powder (100 mesh) were added all at once. The mixture was then warmed to 70° and a solution of 1.7 ml of 12N hydrochloric acid in 8.3 ml absolute ethanol were added. A vigorous exotherm resulted and a strong reflux occurred that persisted for 1.5 hours. When the exotherm subsided, a mixture of 290 ml of 12N HCl and 1400 ml of absolute ethanol were added over 30 minutes. Heat was applied and the mixture was 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 was stirred for 1 hour and filtered. The cake was washed with 1,000 ml of absolute ethanol, the filtrates were combined and the solvent was removed. The remaining solid was 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 was then warmed to 70°
  2. customA vigorous exotherm resulted
  3. temperaturea strong reflux
  4. additionwere added over 30 minutes
  5. temperatureHeat
  6. temperaturethe mixture was refluxed for 2 hours
  7. stirringThe suspension was stirred for 1 hour
  8. filtrationfiltered
  9. washThe cake was washed with 1,000 ml of absolute ethanol
  10. customthe solvent was 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-8b44cb1003f9417f8ab4d886b25c967b
Source dataset
uspto-grants-1984_07
Patent number
US04460508

Reaction notes

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