Hydracrylonitrile → HCID 22725151, compound

HRID 2086903Notes

Reaction equation

HRID 2086903 reaction equation
[N+](C1C=C[C:7]([CH:10]=[C:11](C(=O)C)[CH2:12][C:13]([O:15][CH2:16][CH2:17][C:18]#[N:19])=[O:14])=CC=1)([O-])=O.C(CC(OCC)=O)(=[O:26])CC.OCCC#N>C(O)C>[C:11]([CH2:12][C:13]([O:15][CH2:16][CH2:17][C:18]#[N:19])=[O:14])(=[O:26])[CH2:10][CH3:7]

Participants

5

Reactant 3

HCID 8011HydracrylonitrileHCID 78656Ethyl 3-oxovalerateHCID 54149837HCID 54149837, compound

Product 1

HCID 22725151HCID 22725151, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
202.5 °C

Procedure

2-Cyanoethyl 3-{(4-nitrophenyl)methylene}-4-oxopentanoate. A mixture of ethyl propionylacetate (25 g, 0.173 mol) and 3-hydroxypropionitrile (18.48 g, 0.26 mol) was stirred and heated at 200-205° C. for 2 hours and the ethanol formed was removed by distillation. The residue was subjected to high vacuum distillation and the fraction distilling at 120-125° C. at 0.4 mm Hg was collected to get 2-cyanoethyl propionylacetate (21.5 g, 73.4%). A mixture of 4-nitrobenzaldehyde (14.46 g, 0.957 mol), 2-cyanoethyl propionylacetate (17.0 g, 0.1005 mol), piperidine (0.41 g, 476 mL, 4.8 mmol), and acetic acid (0.288 g, 274 mL, 4.8 mmol) in 2-propanol (400 mL) was stirred at room temperature for 24 h. The white solid, 2-cyanoethyl 3-{(4-nitrophenyl)methylene}-4-oxopentanoate, was filtered, washed with 2-propanol (2×50 mL) dried and used without further purification (Yield: 28.34 g, 97%); m.p. 98-100° C.

Workup

  1. customwas removed by distillation
  2. distillationThe residue was subjected to high vacuum distillation
  3. distillationthe fraction distilling at 120-125° C. at 0.4 mm Hg
  4. customwas collected

Sources & evidence

ORD record
ord-647dece9b12144e590dc617f2b695614
Source dataset
uspto-grants-2004_04
Patent number
US06727257B1

Reaction notes

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