Water → Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid ethyl ester

HRID 861321Notes

Reaction equation

HRID 861321 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([CH:8]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[N:6][OH:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][C:36]([Cl:42])=[CH:37][CH:38]=2)[N:33]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]([CH:8]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][C:36]([Cl:42])=[CH:37][CH:38]=3)[N:33]=2)=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][C:36]([Cl:42])=[CH:37][CH:38]=3)[N:33]=2)=[CH:11][CH:10]=1)=[N:6][OH:7])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 102441602-(Bromomethyl)-7-chloroquinolineHCID 86752019Bis(4-hydroxyphenyl)methyloximinoacetic acid ethyl ester

Product 1

HCID 86752020Bis(4-(7-chloro-2-quinolylmethoxy)phenyl)methyloximinoacetic acid ethyl esterYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution in dry DMF (20 mL) of bis(4-hydroxyphenyl)methyloximinoacetic acid ethyl ester (0.64 g, 2 mmol), prepared as in step 1, was added cesium carbonate (1.6 g, 5 mmol), the mixture was stirred for 10 mutes, and 2-bromomethyl-7-chloroquinoline (1 g, 4 mmol) was added. After stirring for 18 hours, the mixture was poured into water and the precipitated solid was collected by filtration, washed with water, and dried in vacuo. Chromatography on silica gel (hexane/EtOAC 3:1) afforded bis(4-(7-chloro-2-quinolylmethoxy)phenyl)-methyloximinoacetic acid ethyl ester (1.1 g).

Workup

  1. additionwas added
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0b6aae6284cd4b2e9427d4152485a3ea
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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