Dimethylformamide dimethyl acetal → HCID 54299500, compound

HRID 1875693Notes

Reaction equation

HRID 1875693 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH3:16])[CH:15]=[CH:2][C:1]([C:4]1[CH:5]=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 54299500HCID 54299500, compound

Procedure

A homogeneous mixture of 3-acetyl-6-chloropyridine (5 mL) (which can be prepared in a similar manner by the methods disclosed in Lee, C-H. et al., J. Med. Chem. (2001), Vol. 44, pp. 2133-2138) in N,N-dimethylformamide dimethylacetal (15 mL) was refluxed for 4 h. After cooling the reaction mixture to ambient temperature, it was diluted with hexanes (100 mL), sonicated for 30 seconds and the solid formed was isolated by filtration. The resulting solid was then washed with hexanes (3×25 mL), dried and analyzed to afford 3-(3-(dimethylamino)prop-2-en-1-onyl)-6-chloropyridine; LCMS: purity: 92%; MS (m/e): 212 (MH+).

Workup

  1. customcan be prepared in a similar manner by the methods
  2. customsonicated for 30 seconds
  3. customthe solid formed
  4. customwas isolated by filtration
  5. washThe resulting solid was then washed with hexanes (3×25 mL)
  6. customdried

Sources & evidence

ORD record
ord-bae50b5961c3443a8504fb429008a10e
Source dataset
uspto-grants-2012_11
Patent number
US08309566B2

Reaction notes

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