Acetic Acid → HCID 86586634, compound

HRID 322196Notes

Reaction equation

HRID 322196 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH:11]1[C:16](=[O:17])[O:15][C:14]([CH3:19])(C)O[C:12]1=O)=[O:10])=[N+:2]=[N-:3].OCC[C:24]#[N:25].C(=O)=O.[N+:29]([C:32]1[CH:39]=[CH:38][C:35](C=O)=[CH:34][CH:33]=1)([O-:31])=[O:30].N1CCCCC1.C(O)(=O)C>CC(O)C>[C:24]([CH2:19][CH2:14][O:15][C:16](=[O:17])[C:11](=[CH:12][C:35]1[CH:38]=[CH:39][C:32]([N+:29]([O-:31])=[O:30])=[CH:33][CH:34]=1)[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])#[N:25]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 5414-NitrobenzaldehydeHCID 8011HydracrylonitrileHCID 8082PiperidineHCID 23004045HCID 23004045, compound

Product 1

HCID 86586634HCID 86586634, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(6-Azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was heated with 3-hydroxypropionitrile (8.90 g, 125 mmol) at 80° C. until no more CO2 was released. The reaction mixture was diluted with 150 ml of 2-propanol and 4-nitrobenzaldehyde (6.30 g, 41.7 mmol), piperidine (178 mg, 2.10 mmol) and acetic acid (125 mg, 2.10 mmol) were added. The mixture was stirred at room temperature for 48 hrs. After the solvent was evaporated, the residue was dissolved into CHCl3 (200 ml), washed with water (150 ml) and brine (150 ml). After drying (Na2SO4) and evaporation of solvent, 8-azido-2-[ (4-nitrophenyl)methylene]-3-oxooctanoic acid 2-cyanoethyl ester was obtained as a brownish oil (17.0 g, 100%).

Workup

  1. additionwere added
  2. customAfter the solvent was evaporated
  3. dissolutionthe residue was dissolved into CHCl3 (200 ml)
  4. washwashed with water (150 ml) and brine (150 ml)
  5. customAfter drying
  6. custom(Na2SO4) and evaporation of solvent

Sources & evidence

ORD record
ord-2a52b47afede4b37912a60232329e390
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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