Acrylonitrile → HCID 11659070, compound

HRID 1445546Notes

Reaction equation

HRID 1445546 reaction equation
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=[O:5].C1N2CCN(CC2)C1.[C:24](#[N:27])[CH:25]=[CH2:26]>C(OCC)C>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:25](=[CH2:26])[C:24]#[N:27])=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 32325682-Chloro-5-phenylnicotinaldehyde

Product 1

HCID 11659070HCID 11659070, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2-Chloro-5-phenylnicotinaldehyde (10 mmol, 2.17 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 (2.68 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-a68eae317972497092a9637370e78cdc
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Reaction notes

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