Potassium Carbonate → 3-(4-Methyl-imidazol-1-yl)-2-nitro-phenylamine

HRID 1472196Notes

Reaction equation

HRID 1472196 reaction equation
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]1[N:20]=[CH:21][NH:22][CH:23]=1>CN(C=O)C>[CH3:18][C:19]1[N:20]=[CH:21][N:22]([C:2]2[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:6]=[CH:7][CH:8]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1010683-Chloro-2-nitroanilineHCID 178418800HCID 178418800, compound

Product 1

HCID 581355043-(4-Methyl-imidazol-1-yl)-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-2-nitro-aniline (CXXI) (1.0 g, 5.8 mmol), potassium carbonate (2.4 g, 17.4 mmol), and 4-methylimidazole in dry DMF was heated overnight at 120° C. under nitrogen. The reaction was cooled and the solvent was evaporated in vacuo. The residue was suspended in a saturated NaHCO3 solution and extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to provide 3-(4-methyl-imidazol-1-yl)-2-nitro-phenylamine (CXXIX). 1H NMR (CDCl3, 400 MHz) δ ppm 2.19 (s, 3H), 6.53 (m, 1H), 6.79 (m, 1H), 6.93 (m, 1H), 7.32 (m, 1H), 7.60 (m, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent was evaporated in vacuo
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f5889a829a434dc8867a8407beb64b75
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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