Methyl Ethyl Ketone → HCID 13386243, compound

HRID 647443Notes

Reaction equation

HRID 647443 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[CH:12]=[C:11]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH3:21])[N:10]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>ClCCl>[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[CH:12]=[C:11]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:24][CH:23]=2)[CH3:21])[N:10]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 133862264-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

Product 1

HCID 13386243HCID 13386243, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-bromoacetate (0.23 g), 4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenol (0.40 g), anhydrous potassium carbonate (0.19 g) and methyl ethyl ketone was heated under reflux for 12 hrs. The mixture was cooled, diluted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated to give an oil, which was purified by column chromatography over silica gel (eluant dichloromethane) to give ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenoxy}acetate (0.52 g) as a yellow crystalline solid, mp 99° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hrs
  3. temperatureThe mixture was cooled
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give an oil, which
  8. customwas purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-1e931aee8cf8448b8541b54203265d1b
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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