Acrylonitrile → HCID 86612628, compound

HRID 1445549Notes

Reaction equation

HRID 1445549 reaction equation
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=[O:5].C1N2CCN(CC2)C1.[C:26](#[N:29])[CH:27]=[CH2:28]>C(OCC)C>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:27](=[CH2:28])[C:26]#[N:29])=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 154592262-Chloro-5-(4-methoxyphenyl)pyridine-3-carbaldehyde

Product 1

HCID 86612628HCID 86612628, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2-Chloro-5-(4-methoxyphenyl)-nicotinaldehyde (10 mmol, 2.45 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 (2.99 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-531545f7854345358a1b847728e89fa9
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Reaction notes

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