m-Formylbenzonitrile → HCID 67980174, compound

HRID 1047193Notes

Reaction equation

HRID 1047193 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>[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

5

Reactant 3

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

Product 1

HCID 67980174HCID 67980174, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
130 °C

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 1000 ml of acetic anhydride, and the resulted mixture solution is stirred and heated to 125-135° C. for 24 hours. After distilling out the most of acetic anhydride, 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 266.8 g of the title compound, with a yield of 92%.

Workup

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

Sources & evidence

ORD record
ord-607fc26cab4647e4873ce22425fa60d9
Source dataset
uspto-grants-2013_10
Patent number
US08569508B2

Reaction notes

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