2,5-Dichloropyridine-4-carbonitrile → N-(2,5-Dichloro-pyridin-4-ylmethyl)-acetamide

HRID 1819487Notes

Reaction equation

HRID 1819487 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[C:8]#[N:9].[CH3:11][C:12](OC(C)=O)=[O:13].CC(O)=O>O=[Pt]=O>[Cl:10][C:5]1[CH:6]=[C:7]([CH2:8][NH:9][C:12](=[O:13])[CH3:11])[C:2]([Cl:1])=[CH:3][N:4]=1

Participants

4

Reactant 2

HCID 135602102,5-Dichloropyridine-4-carbonitrileHCID 21895370AcOH AcOAc

Product 1

HCID 57885548N-(2,5-Dichloro-pyridin-4-ylmethyl)-acetamideYield 40%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of 3,6-dichloro-4-cyanopyridine (prepared according to WO 9633975) (3.40 g, 19.65 mmol) and PtO2 (0.40 g) in 1:1 Ac2O/AcOH (60 mL) was shaken in a Parr hydrogenation apparatus at 30 psi H2 for 6 h. The reaction mixture was filtered through a pad a celite and the filtered solids washed with EtOAc. The combined filtrate and washings were concentrated in vacuo and the resulting white solid purified by column chromatography on a 120 g ISCO combi-flash cartridge (silica gel, 20:80 to 100:0 EtOAc/hexane) to afford N-(2,5-Dichloro-pyridin-4-ylmethyl)-acetamide (1.73 g, 40%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad a celite
  2. washthe filtered solids washed with EtOAc
  3. concentrationThe combined filtrate and washings were concentrated in vacuo
  4. customthe resulting white solid purified by column chromatography on a 120 g ISCO combi-flash cartridge (silica gel, 20:80 to 100:0 EtOAc/hexane)

Sources & evidence

ORD record
ord-b346a9dbe47d444aa619666c90f2f766
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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