Water → 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

HRID 1669391Notes

Reaction equation

HRID 1669391 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[NH:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[C:16]([CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O)#[N:17].N1CCCCC1.O>C(Cl)(Cl)Cl.CN(C)C=O>[OH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5](=[O:15])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH2:18][C:16]#[N:17])[CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 47669982-(3-Formylphenoxy)acetonitrileHCID 546825123-Acetyl-2,4-dihydroxyquinoline

Product 1

HCID 673471754-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinoneYield 75.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

In a mixture of 3000 ml of chloroform and 600 ml of dimethylformamide were dissolved 60.00 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 142.20 g of 3-(cyanomethoxy)benzaldehyde and 17.64 g of piperidine, and the solution was heated overnight under reflux while water was removed with a Soxhlet extractor filled with molecular sieves. After cooled to room temperature, precipitated crystals were filtered, and washed with 750 ml of tetrahydrofuran and 900 ml of t-butyl methyl ether to obtain 77.59 g of 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (10e)] as a yellow crystal.

Workup

  1. temperaturethe solution was heated overnight
  2. customwas removed with a Soxhlet extractor
  3. additionfilled with molecular sieves
  4. customprecipitated crystals
  5. filtrationwere filtered
  6. washwashed with 750 ml of tetrahydrofuran and 900 ml of t-butyl methyl ether

Sources & evidence

ORD record
ord-3f95767ae01a4e08967f9730d91b159c
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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