4-Nitrobenzaldehyde → 2-((4-Nitrophenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl ester

HRID 322175Notes

Reaction equation

HRID 322175 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][C:21]#[N:22])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>CC(O)C.N1CCCCC1.C(O)(=O)C>[C:21]([CH2:20][CH2:19][O:18][C:12](=[O:17])[C:13](=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:14](=[O:15])[CH3:16])#[N:22]

Participants

6

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 123604062-Cyanoethyl 3-oxobutanoate

Product 1

HCID 543622242-((4-Nitrophenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl esterYield 59%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of 4-nitrobenzaldehyde (10.00 g, 66.2 mol), 2-cyanoethyl acetoacetate (10.27 g, 66.2 mol), piperidine (281 mg, 3.31 mmol) and acetic acid (198 mg, 3.31 mmol) in 250 ml of 2-propanol was stirred at room temperature for 48 hrs. Reaction mixture was filtered, the solid collected and dried in air to give 2-[(4-nitrophenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl ester as a white powder (11.24 g, 59%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered
  3. customthe solid collected
  4. customdried in air

Sources & evidence

ORD record
ord-5294dab59e4c42679cb0a66c837a4ede
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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