Water → 2,4-Dichloro-5-methylpyridine

HRID 1992648Notes

Reaction equation

HRID 1992648 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH2:9]Cl)=[CH:4][N:3]=1.C(N(CC)CC)C.O>C(O)C.[Ni].CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 27627282,4-Dichloro-5-(chloromethyl)pyridine

Product 1

HCID 126437182,4-Dichloro-5-methylpyridine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Dichloro-5-chloromethyl-pyridine (1.43 g, 7.28 mmol) is dissolved in ethanol (14 ml). After addition of triethyl amine (737 mg, 7.28 mmol), Raney nickel (143 mg) is added. The reaction vessel is connected to a balloon filled with H2. After 3 hours of very vigorous magnetically stirring at RT, NMR analysis of a reaction aliquot indicated complete conversion of the starting material. The reaction mixture is diluted with EtOAc and poured into water.

Workup

  1. additionis added
  2. additionfilled with H2
  3. customNMR analysis of a reaction aliquot indicated complete conversion of the starting material

Sources & evidence

ORD record
ord-79a391b269bb465b85cdd312f2bedf29
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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