Ammonium Hydroxide → HCID 13457348, compound

HRID 463292Notes

Reaction equation

HRID 463292 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[NH4+]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 20282214HCID 20282214, compound

Product 1

HCID 13457348HCID 13457348, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above nitro compound (2.00 g) was added to a stirred suspension of finely ground ferrous ammonium sulphate hexahydrate and the mixture heated to reflux. Concentrated ammonium hydroxide was added every two minutes in two ml aliquots until thin layer chromatography showed the reaction to be complete. Absolute ethanol (150 ml) was then added and the reaction mixture filtered through Celite. After evaporation of the solvent the residue was chromatographed on silica gel eluting with 5% methanol in methylene chloride to give 1-[2-(4-aminophenoxy)-3,3-dimethyl-n-butyl]imidazole (1.4 g) as an oil. This was converted to the bis hydrochloride salt as described in Example 16, the salt being recrystallized from ethyl acetate methanol with m.p. 265°-270° C. (dec.).

Workup

  1. temperaturethe mixture heated to reflux
  2. customthe reaction
  3. filtrationthe reaction mixture filtered through Celite
  4. customAfter evaporation of the solvent the residue
  5. customwas chromatographed on silica gel eluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-fb4d0ca6b6714a60a37adb4375861a58
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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