Sodium Hydroxide → Imidazole

HRID 1199523Notes

Reaction equation

HRID 1199523 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].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 2

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

Product 2

HCID 795ImidazoleHCID 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)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-cd08fa98413b4da98c9b9e79ad135510
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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