Hydrazine → HCID 178434352, compound

HRID 1046484Notes

Reaction equation

HRID 1046484 reaction equation
[Cl:1][C:2]1[C:7]([C:8](=O)[CH3:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:12][NH2:13]>CCOC(C)=O.O>[Cl:1][C:2]1[C:7]2[C:8]([CH3:9])=[N:12][NH:13][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 534024421-(2,4-Dichloropyridin-3-yl)ethan-1-one

Product 1

HCID 178434352HCID 178434352, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2,4-Dichloro-pyridin-3-yl)-ethanone (6.2 g, 32.6 mmol) in 65% aqueous hydrazine (45 ml) was stirred at rt overnight. The mixture was diluted with EtOAc and water. The organic extract was washed with brine, dried and concentrated to give a white solid. The crude product was purified by flash column chromatography over silica gel (200 g) eluting with 1:1 petroleum ether:EtOAc to give an off-white solid (3.5 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.64 (s, 3 H), 7.47 (d, J=5.95 Hz, 1 H), 8.06 (d, J=5.95 Hz, 1 H). m/z (ES+APCI)+: 168/170 [M+H]+.

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe crude product was purified by flash column chromatography over silica gel (200 g)
  7. washeluting with 1:1 petroleum ether

Sources & evidence

ORD record
ord-039190ea76dc41b2ab4f71516e2c9086
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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