Ethyl Acetate → HCID 21891959, compound

HRID 2414934Notes

Reaction equation

HRID 2414934 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-312767d8ddc24c348f452661bd918c3d
Source dataset
uspto-grants-2004_11
Patent number
US06815546B2

Reaction notes

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