Ethyl cyanoacetate → HCID 16077534, compound

HRID 2095775Notes

Reaction equation

HRID 2095775 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[C:10]([CH2:12][C:13](OCC)=[O:14])#[N:11]>CCCCCC.C(OCC)(=O)C>[C:10]([CH2:12][C:13]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=1[CH3:9])=[O:14])#[N:11]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 679824-Fluoro-2-methylaniline

Product 1

HCID 16077534HCID 16077534, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
150 °C

Procedure

4-Fluoro-2-methylaniline (3.9 g, 31 mmol) was added to ethyl cyanoacetate (5.3 g, 46 mmol) and the mixture was stirred at 150° C. for 4 hr. After cooling to room temperature, hexane-ethyl acetate was added to the reaction mixture, and the precipitate was collected by filtration to give the title compound (4.0 g, 67%) as a pale-yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4e12ef2df2eb41d78ba09d71faeb1ac8
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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