3-Chloro-6-vinylpyridazine → 3-Chloro-6-ethylpyridazine

HRID 655258Notes

Reaction equation

HRID 655258 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH:8]=[CH2:9])=[CH:6][CH:7]=1>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 223362693-Chloro-6-vinylpyridazine

Product 1

HCID 205394953-Chloro-6-ethylpyridazineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chloro-6-vinyl-pyridazine (1 g, 7.09 mmol), palladium on carbon (10% wt, 200 mg) in ethyl acetate (14 mL) under a hydrogen atmosphere was stirred vigorously at ambient temperature for 4 hours. The mixture was then filtered through a pad of celite and the filtrate concentrated onto silica gel and purified via flash column chromatography (SiO2, hexane:ethyl acetate 90:10-50:50) to return the title compound as a white solid (627 mg, 63% yield). 1H NMR (CDCl3): δ 1.27 (3H, t), 2.93 (2H, q), 7.72 (1H, d), 7.83 (1H, d). MS m/z=143 (M+H+)+.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationthe filtrate concentrated onto silica gel
  3. custompurified via flash column chromatography (SiO2, hexane:ethyl acetate 90:10-50:50)

Sources & evidence

ORD record
ord-159ec85394cf421283488394ac85f800
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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