Dimethylformamide → 6-Methoxy-2-(4-methyl-2-propyl-imidazol-1-yl)-3-nitro-pyridine

HRID 1986601Notes

Reaction equation

HRID 1986601 reaction equation
[OH-].[K+].[CH3:3][C:4]1[N:5]=[C:6]([CH2:9][CH2:10][CH3:11])[NH:7][CH:8]=1.CN(C)C=O.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([O:27][CH3:28])[N:19]=1>O>[CH3:28][O:27][C:20]1[N:19]=[C:18]([N:7]2[CH:8]=[C:4]([CH3:3])[N:5]=[C:6]2[CH2:9][CH2:10][CH3:11])[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 178440092HCID 178440092, compound

Product 1

HCID 468319366-Methoxy-2-(4-methyl-2-propyl-imidazol-1-yl)-3-nitro-pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension prepared of 20.0 g KOH (solid), 25.8 g 4-methyl-2-propyl imidazole and 130 ml dimethyl formamide were added 38.0 g 2-chloro-6-methoxy-3-nitro pyridine in small amounts at a reaction temperature of 5° C. The reaction mixture was stirred for 75 minutes at room temperature. Then the reaction mixture was poured in 600 ml water. The mixture was further stirred for 1 hr. The desired product precipitated during this time. The resulting solid was collected by filtration, washed with 100 ml water for 3 times and dried in a dry box with vacuum (40° C.).

Workup

  1. stirringThe mixture was further stirred for 1 hr
  2. customThe desired product precipitated during this time
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with 100 ml water for 3 times
  5. customdried in a dry box with vacuum (40° C.)

Sources & evidence

ORD record
ord-c34e5664565b46b1b13fc426897c24a7
Source dataset
uspto-grants-2009_06
Patent number
US07550465B2

Reaction notes

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