Dichloromethane → Ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionate

HRID 647447Notes

Reaction equation

HRID 647447 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].ClCCl>C(C(C)=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:18]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13386245HCID 13386245, compound

Product 1

HCID 20484883Ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-[(7-chloroisoquinolin-3-yl)oxy]phenol (2.82 g) and ethyl 2-bromopropionate (2.07 g) in the presence of anhydrous potassium carbonate (1.58 g) were refluxed in methyl ethyl ketone (50 ml) for 4 hrs. The mixture was cooled, poured into dichloromethane, washed with water, dried (MgSO4) and evaporated. Purification by column chromatography over silica gel (eluant dichloromethane) gave ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionate (3.33 g) as a brown oil.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-ba578d89083c44f7a4185db7a988dd9b
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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