Acetic Anhydride → HCID 67980174, compound

HRID 1047194Notes

Reaction equation

HRID 1047194 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>CN(C=O)C>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=[CH:6][C:5]3[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=3)[C:1]#[N:2])=[N:19]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 90670m-FormylbenzonitrileHCID 1383957-Chloro-2-methylquinolineHCID 517045Sodium Acetate

Product 1

HCID 67980174HCID 67980174, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under the protection by nitrogen, meta-cyanobenzaldehyde (137.6 g, 1.05 mol), 7-chloroquinaldine (177 g, 1.0 mol) and sodium acetate (82 g) are added into 200 ml of acetic anhydride and 800 ml of dimethyl fomamide (DMF), and the resulted mixture solution is stirred and heated to reflux for 24 hours. After distilling the most solvent, 300 ml of water is added into the residue, and then extracted by ethyl acetate (500 ml×3), washed with saturated saline water, dried with anhydrous sodium sulfate and condensed in the vacuum. The resulted residue is then purified through Flash Column Chromatography to obtain 241 g of the title compound, with a yield of 83%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. distillationAfter distilling the most solvent, 300 ml of water
  4. additionis added into the residue
  5. extractionextracted by ethyl acetate (500 ml×3)
  6. washwashed with saturated saline water
  7. dry with materialdried with anhydrous sodium sulfate and condensed in the vacuum
  8. customThe resulted residue is then purified through Flash Column Chromatography

Sources & evidence

ORD record
ord-1067d26e78d54febaa79c191a11aab1b
Source dataset
uspto-grants-2013_10
Patent number
US08569508B2

Reaction notes

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