Sodium Hydroxide → 4-(1H-Imidazol-1-yl)-2-methylaniline

HRID 568377Notes

Reaction equation

HRID 568377 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[OH-].[Na+]>C(O)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 144502461-(3-Methyl-4-nitrophenyl)-1H-imidazole

Product 1

HCID 144502604-(1H-Imidazol-1-yl)-2-methylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (55.0 g) was added portionwise to a stirred suspension of 1-(3-methyl-4-nitrophenyl)imidazole (10.0 g) in absolute ethanol (100 cm3). After heating under reflux for 4 hours, the cooled mixture was basified to pH8 with aqueous 2.5M sodium hydroxide solution and filtered. The filtrate was evaporated in vacuo, partitioned between chloroform (100 cm3) and water (50 cm3), and the aqueous phase was further extracted with chloroform (3×50 cm3). The combined and dried (MgSO4) extracts were concentrated in vacuo to give a solid which was recrystallised from ethyl acetate to afford 1-(4-amino-3-methylphenyl)imidazole, m.p. 131°-134°, (4.7 g).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. custompartitioned between chloroform (100 cm3) and water (50 cm3)
  6. extractionthe aqueous phase was further extracted with chloroform (3×50 cm3)
  7. dry with materialdried (MgSO4) extracts
  8. concentrationwere concentrated in vacuo
  9. customto give a solid which
  10. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3bcfb2fdc70c49308195198d2d774698
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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