Ammonium Chloride → HCID 58201192, compound

HRID 2093540Notes

Reaction equation

HRID 2093540 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([CH3:12])[C:3]=1[Cl:13].[CH3:14][O-:15].[Na+].[Cl-].[NH4+]>CO>[Cl:13][C:3]1[C:4]([CH3:12])=[N:5][CH:6]=[C:7]([C:2]=1[O:15][CH3:14])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 58201215Methyl 4,5-dichloro-6-methyl-3-pyridinecarboxylate

Product 1

HCID 58201192HCID 58201192, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude methyl 4,5-dichloro-6-methylnicotinate (380 mg) was dissolved in 3 ml of methanol and, in a nitrogen stream, sodium methoxide (120 mg) was then added to the solution under cooling on ice. The temperature of the reaction solution was gradually raised to room temperature, and it was stirred for 18 hours. After the disappearance of the materials had been confirmed, a saturated ammonium chloride aqueous solution was added to the reaction solution under cooling on ice, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away. The residue was purified by silica gel chromatography (ethyl acetate-hexane), so as to obtain the title compound (210 mg) as a solid.

Workup

  1. additionwas then added to the solution
  2. temperatureunder cooling on ice
  3. temperatureunder cooling on ice
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled away
  7. customThe residue was purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3b981c7fc49f4ac9be9447b1d7e017c8
Source dataset
uspto-grants-2013_05
Patent number
US08445504B2

Reaction notes

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