Methyl cyanoacetate → HCID 86584083, compound

HRID 2213836Notes

Reaction equation

HRID 2213836 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=O)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1.[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#[N:19].N1CCCCC1>CO>[C:18](/[C:20](=[CH:9]\[C:8]1[CH:11]=[C:12]([O:13][CH3:14])[C:5]([O:4][CH2:3][CH2:2][Cl:1])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])/[C:21]([O:23][CH3:24])=[O:22])#[N:19]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 219563824-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde

Product 1

HCID 86584083HCID 86584083, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3.00 g (11.58 mmol) of 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzaldehyde and 1.5 mL (16.95 mmol) of methyl cyanoacetate in 30 mL of methanol is added 0.3 mL of piperidine. The mixture is heated at reflux for 5 minutes then cooled slightly and the thick suspension is collected by filtration washing with ethyl acetate followed by diethyl ether to give 1.07 g (27%) of methyl (2E)-2-cyano-3-[4-(2-chloroethoxy)-5-methoxy-2-nitrophenyl]-2-propenoate as a yellow solid, mp softens at 121° C., melts at 157–160° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5 minutes
  3. temperaturethen cooled slightly
  4. filtrationthe thick suspension is collected by filtration
  5. washwashing with ethyl acetate

Sources & evidence

ORD record
ord-80b1110cc9484ff6a9680e57077d3ee0
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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