Acetic Acid → HCID 54530594, compound

HRID 396675Notes

Reaction equation

HRID 396675 reaction equation
[C:1]([CH2:8][C:9]([O:11][CH2:12][CH2:13][C:14]#[N:15])=[O:10])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17].N1CCCCC1.C(O)(=O)C>CC(O)C>[C:14]([CH2:13][CH2:12][O:11][C:9](=[O:10])[C:8](=[CH:23][C:22]1[CH:25]=[CH:26][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)[C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])#[N:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 8082PiperidineHCID 23004120HCID 23004120, compound

Product 1

HCID 54530594HCID 54530594, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-cyanoethyl hexanoylacetate (21.1 g, 100 mmol), 4-nitrobenzaldehyde (16.6 g, 110 mmol), piperidine (430 mg, 5.00 mmol) and acetic acid (300 mg, 5.00 mmol) in 350 ml of 2-propanol was stirred at room temperature for 48 hrs. The resulting white precipitate was filtered and dried in the air. The product, 2-[(4-nitrophenyl)methylene]-3-oxooctanoic acid 2-cyanoethyl ester was obtained as a white powder (25.2 g, 73% yield).

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. customdried in the air

Sources & evidence

ORD record
ord-f08f63f46c9c41308039bb9cac606171
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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