Oxalic Acid → HCID 86698213, compound

HRID 76328Notes

Reaction equation

HRID 76328 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][C:15]#[N:16].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>C(O)C.C(OCC)(=O)C>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[C:2]([CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][CH2:15][NH:16][CH2:19][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])#[N:1]

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 8821Ethyl AcrylateHCID 86698210[2-(2-Aminoethyl)-4,5-dimethoxyphenyl]acetonitrile

Product 1

HCID 86698213HCID 86698213, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [2-(2-aminoethyl)-4,5-dimethoxyphenyl]acetonitrile (6.5 g, 29.5 mmol) and ethyl acrylate (3.9 ml, 36 mmol, 1.2 eq.) in 120 mL of ethanol is stirred for 20 hours at ambient temperature. The reaction mixture is subjected to drying in vacuo; then the crude reaction mixture is taken up in a mixture of ethyl acetate (133 mL) and ethanol (13 mL) and is heated at reflux in the presence of oxalic acid (2.52 g, 28 mmol, 0.95 eq.). Precipitation from the mixture occurs during contact at reflux. After returning to ambient temperature, the mixture is filtered and washed with 19 ml of ethyl acetate to obtain a white powder (9 g) corresponding to the title compound.

Workup

  1. customto drying in vacuo
  2. customthen the crude reaction mixture
  3. temperatureis heated
  4. customPrecipitation from the mixture
  5. temperatureat reflux
  6. customAfter returning to ambient temperature
  7. filtrationthe mixture is filtered
  8. washwashed with 19 ml of ethyl acetate

Sources & evidence

ORD record
ord-ffe6fd77ae514465844de9ee9ab2dd45
Source dataset
uspto-grants-2014_09
Patent number
US08835627B2

Reaction notes

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