Methyl cyanoacetate → HCID 69372057, compound

HRID 989385Notes

Reaction equation

HRID 989385 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=O)=[CH:8][C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([O-:3])=[O:2].[C:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])#[N:17].N1CCCCC1>CO>[C:16]([C:18](=[CH:10][C:9]1[CH:8]=[C:7]([O:12][CH3:13])[C:6]([O:14][CH3:15])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])[C:19]([O:21][CH3:22])=[O:20])#[N:17]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 885056-Nitroveratraldehyde

Product 1

HCID 69372057HCID 69372057, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 7.00 g (33.15 mmol) of 6-nitroveratraldehyde (80%) and 3.4 mL (38.42 mmol) of methyl cyanoacetate in 70 mL of methanol is added 0.7 mL of piperidine. An additional 100 mL of methanol is added and the thick suspension is warmed slightly until the mixture stirred freely. After stirring at room temperature for 1 hour, the solids are collected by filtration washing with methanol followed by diethyl ether to give 7.57 g (78%) of methyl 2-cyano-3-(4,5-dimethoxy-2-nitrophenyl)-2-propenoate as a pale yellow solid, mp 162-164° C.

Workup

  1. temperaturethe thick suspension is warmed slightly until the mixture
  2. stirringAfter stirring at room temperature for 1 hour
  3. filtrationthe solids are collected by filtration
  4. washwashing with methanol

Sources & evidence

ORD record
ord-e038417aa8df4a908962cf694c87813c
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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