Potassium Carbonate → HCID 20484903, compound

HRID 647444Notes

Reaction equation

HRID 647444 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=2)[CH:14]=[C:13]([N:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[CH3:23])[N:12]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:8][C:2]([O:30][C:27]1[CH:26]=[CH:25][C:24]([N:22]([C:13]2[N:12]=[C:11]([Cl:10])[C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=3)[CH3:23])=[CH:29][CH:28]=1)([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 133862264-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

Product 1

HCID 20484903HCID 20484903, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-bromo-2-methylpropionate (0.54 g), 4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenol (0.74 g), potassium carbonate (0.38 g) dimethylformamide was heated at 100° C. for 28 hrs. The mixture was cooled, diluted with dichloromethane, washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated to give an oil, which was purified by column chromatography over silica gel (eluent dichloromethane) to give ethyl 2-methyl-2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]-phenoxy}propionate (0.55 g) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customto give an oil, which
  6. customwas purified by column chromatography over silica gel (eluent dichloromethane)

Sources & evidence

ORD record
ord-7e2805c655b84d7b973873a010d380a1
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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