Potassium Carbonate → HCID 20484899, compound

HRID 647422Notes

Reaction equation

HRID 647422 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([N:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH3:21])[N:16]=[CH:17]2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([N:20]([C:22]3[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]=3)[CH3:21])[N:16]=[CH:17]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13386231HCID 13386231, compound

Product 1

HCID 20484899HCID 20484899, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 2-bromopropionate (0.64 g), 4-[N-(7-chloroisoquinolin-3-yl)-N-methylamino]phenol (0.92 g), anhydrous potassium carbonate (0.49 g) and methyl ethyl ketone was heated under reflux for a period of 5 hours. The solution was cooled, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the product was purified by column chromatography over silica gel (eluant dichloromethane) to give ethyl 2-{4-[N-(7-chloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.00 g) as a green oil. The assigned structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.25 (3H, t); 1.60 (3H, d); 3.45 (3H, s); 4.22 (2H, q); 4.75 (1H, q); 6.52 (1H, s); 6.8-7.4 (6H, m); 7.62 (1H, m); 8.75 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 5 hours
  3. temperatureThe solution 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. customthe product was purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-0e59063910f0422ebac88e6e82d80aad
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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