Sodium Hydroxide → HCID 19867080, compound

HRID 649541Notes

Reaction equation

HRID 649541 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:17])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=2)[CH:6]=1.[OH-].[Na+]>C(O)C>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]2[CH:6]=[C:2]([I:1])[N:3]=[C:4]2[CH3:17])=[CH:8][C:9]=1[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 198670994-Iodo-2-methyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole

Product 1

HCID 19867080HCID 19867080, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (9.04 g) was added portionwise to a stirred suspension of 4-Iodo-1-(3-methyl-4-nitrophenyl)-2-methylimidazole (2.75 g) in absolute ethanol (50 cm3) under nitrogen. After heating under reflux for 1 hour, the cooled mixture was basified to pH8 with aqueous 2.5M sodium hydroxide, and extracted with chloroform (3×100 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:dichloromethane, 1:25 by volume. Combination and evaporation of appropriate fractions afforded the title compound as a crude oil (2.41 g), which was used directly without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with chloroform (3×100 cm3)
  4. dry with materialdried (MgSO4) organic extracts
  5. customwere evaporated in vacuo
  6. customto give a residue which
  7. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with methanol
  9. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-9cc52b6f52fa472e827a5cc454a12641
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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