Potassium Carbonate → HCID 13386227, compound

HRID 647420Notes

Reaction equation

HRID 647420 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[CH:13]=[C:12]([N:21]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH3:22])[N:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[CH:13]=[C:12]([N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:25][CH:24]=2)[CH3:22])[N:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 133862264-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

Product 1

HCID 13386227HCID 13386227, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 2-bromopropionate (1.6 g), 4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenol (2.76 g), anhydrous potassium carbonate (1.19 g) and methyl ethyl ketone was heated under reflux for a period of 3 hours. The mixture was cooled, washed with water and was 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 give ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (3.10 g) as a yellow oil which crystallised from ethanol, mp 86° C. The assigned structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.3 (3H, t); 1.65 (3H, d); 3.45 (3H, s); 4.25 (2H, q); 4.75 (1H, q); 6.40 (1H, s); 6.85-7.35 (6H, m); 8.00 (1H, s).

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 materialwas dried 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-3ecfa5ece3a24bfcbef511c66fa2d553
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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