Hydracrylonitrile → HCID 22725151, compound

HRID 1586119Notes

Reaction equation

HRID 1586119 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])[CH2:2][CH3:3].OCC[C:14]#[N:15]>C(O)C>[C:1]([CH2:5][C:6]([O:8][CH2:9][CH2:10][C:14]#[N:15])=[O:7])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 8011HydracrylonitrileHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 22725151HCID 22725151, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
202.5 °C

Procedure

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-fa1385cd81c045bf88322a060bc1d43c
Source dataset
uspto-grants-1999_08
Patent number
US05942517

Reaction notes

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