Potassium Carbonate → HCID 178472169, compound

HRID 647436Notes

Reaction equation

HRID 647436 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH3:21])[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:24][CH:23]=2)[CH3:21])[N:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 178482208HCID 178482208, compound

Product 1

HCID 178472169HCID 178472169, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 2-bromopropionate (1.36 g), 4-[N-(1-hydroxyisoquinolin-3-yl)-N-methylamino]phenol (2.00 g), anhydrous potassium carbonate (1.04 g) and methyl ethyl ketone (20 ml) was heated under reflux for a period of 3 hours. The mixture was cooled, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give an oil, which was purified by column chromatography over silica gel (eluant dichloromethane to yield ethyl 2-{4-[N-(1-hydroxyisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.92 g) as a brown solid mp 96° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 3 hours
  3. temperatureThe mixture was cooled
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customto give an oil, which
  8. customwas purified by column chromatography over silica gel (eluant dichloromethane

Sources & evidence

ORD record
ord-d4593d91650749c59fe1a3b4dc8789a2
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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