Acrylonitrile → HCID 44405354, compound

HRID 1445547Notes

Reaction equation

HRID 1445547 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].C1N2CCN(CC2)C1.[C:22](#[N:25])[CH:23]=[CH2:24]>C(OCC)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:12]([OH:13])[C:23]([C:22]#[N:25])=[CH2:24]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 11629787HCID 11629787, compound

Product 1

HCID 44405354HCID 44405354, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of Methyl 6-chloro-5-formyl-2-pyridincarboxylate (10 mmol, 1.99 g) and DABCO (10 mmol. 1.12 g) was added an acrylonitrile (60 mmol.) under neat conditions [solvent free conditions] at room temperature and the reaction progress was monitored by TLC. Upon completion of the reaction mixture (˜4-5 min.) was diluted with diethyl ether (300 ml.) and washed with water 3×50 ml. The organic layer was dried over Na2SO4 and concentrated, the residue was subjected to column chromatography over silica gel, eluting with ethyl acetate and hexane (2:8, v/v) to give the desired product in almost quantitative (2.50 g.).

Workup

  1. washwashed with water 3×50 ml
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. washeluting with ethyl acetate and hexane (2:8, v/v)

Sources & evidence

ORD record
ord-caedd17d4fde48209ae9606c545df8ed
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Reaction notes

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