2,6-Dichloro-4-methylpyridine → HCID 84116020, compound

HRID 1908842Notes

Reaction equation

HRID 1908842 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1>C(NCC)C.CC(=O)OCC>[Cl:9][C:4]1[N:3]=[C:2]([N:3]([CH2:4][CH3:5])[CH2:2][CH3:7])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

4

Reactant 1

HCID 108989972,6-Dichloro-4-methylpyridine

Product 1

HCID 84116020HCID 84116020, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 8021DiethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a sealed vial, a solution of 2,6-dichloro-4-picoline (1.80 g, 11.1 mmol) in diethylamine (5 mL) is heated to 135° C. for 40 h in a microwave oven. The pressure in the vial reaches 6.5 bar. The mixture is diluted with EA (200 mL) and washed with 1 N KHSO4, solution. The washings are extracted back with EA (100 mL) and the combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 95:5 to give (6-chloro-4-methyl-pyridin-2-yl)-diethyl-amine (1.15 g) as a colourless solid; LC-MS: tR=1.05 min, [M+1]+=198.97.

Workup

  1. washwashed with 1 N KHSO4, solution
  2. extractionThe washings are extracted back with EA (100 mL)
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 95:5

Sources & evidence

ORD record
ord-31ee763b91f842218f54c16f88582e41
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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