Ethyl Acetate → HCID 21891959, compound

HRID 1007873Notes

Reaction equation

HRID 1007873 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH2:17]Cl)[C:9]2[C:4](=[CH:5][C:6]([Cl:21])=[C:7]([O:19][CH3:20])[CH:8]=2)[N:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(OCC)(=O)C>O>[Cl:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH2:17][N:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:21])=[C:7]([O:19][CH3:20])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 21891992Ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate

Product 1

HCID 21891959HCID 21891959, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2,7-dichloro-4-(chloromethyl)-6-methoxy-3-quinolinecarboxylate (6.9 g, 20 mmol) and N-methylpiperazine (9 ml, 80 mmol) is heated to 60° C. for 30 min. The reaction mass is diluted with water and extraction is carried out with ethyl acetate. After decanting, the organic phase is washed with water, followed by drying over magnesium sulphate, filtering and evaporating under reduced pressure. The residue is taken up in water, agitated for 15 minutes, filtered, washed with water and dried under vacuum. The residue is purified by column chromatography (SiO2, MeOH/CH2Cl2: 5/95 to 8/92). 6.7 g of product, a beige solid, is obtained.

Workup

  1. customAfter decanting
  2. washthe organic phase is washed with water
  3. dry with materialby drying over magnesium sulphate
  4. filtrationfiltering
  5. customevaporating under reduced pressure
  6. filtrationfiltered
  7. washwashed with water
  8. customdried under vacuum
  9. customThe residue is purified by column chromatography (SiO2, MeOH/CH2Cl2: 5/95 to 8/92)

Sources & evidence

ORD record
ord-72f8c3dc15e54e5481f438bf8242d7c8
Source dataset
uspto-grants-2004_09
Patent number
US06797715B1

Reaction notes

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