Pyridine → HCID 18466614, compound

HRID 2229329Notes

Reaction equation

HRID 2229329 reaction equation
[NH2:1][C:2]1[C:3]([Cl:10])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].N1C=CC=CC=1.[Br:17][C:18]1[CH:19]=[C:20]([C:25](Cl)=[O:26])[C:21]([Cl:24])=[N:22][CH:23]=1>C1(C)C=CC=CC=1.O>[Br:17][C:18]1[CH:19]=[C:20]([C:25]([NH:1][C:2]2[C:3]([Cl:10])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=2[CH3:8])=[O:26])[C:21]([Cl:24])=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7010122,6-dichloro-4-methylpyridin-3-amineHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chloride

Product 1

HCID 18466614HCID 18466614, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3-Amino-2,6-dichloro-4-methylpyridine (0.51 g, 2.85 mmol) was dissolved in toluene (35 mL) and pyridine (0.27 mL, 3.28 mmol) was added. 5-Bromo-2-chloro-3-pyridinecarbonyl chloride (0.80 g, 3.14 mmol) was then added dropwise over 30 min. The resulting mixture was stirred at room temperature for 1 h, diluted with water and extracted with toluene (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The resulting thick oil was triturated with CH2Cl2, and the white solid collected via suction filtration to give the title compound (0.41 g, 36% yield).

Workup

  1. extractionextracted with toluene (2×)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting thick oil was triturated with CH2Cl2
  6. filtrationthe white solid collected via suction filtration

Sources & evidence

ORD record
ord-63adb8d9fd6842fba6fc6fa6b267b8e0
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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