Methyl Ethyl Ketone → HCID 20484885, compound

HRID 647432Notes

Reaction equation

HRID 647432 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]([F: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>ClCCl>[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F: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

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 133862374-[N-(1-chloro-7-fluoroisoquinolin-3-yl)-N-methylamino]phenol

Product 1

HCID 20484885HCID 20484885, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-bromopropionate (1.12 g), 4-[N-(1-chloro-7-fluoroisoquinolin-3-yl)-N-methylamino]phenol (1.70 g), anhydrous potassium carbonate (0.86 g) and methyl ethyl ketone (20 ml) was heated under reflux for a period of 3 hours. The mixture was cooled, diluted with dichloromethane, 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 give ethyl 2-{4-[N-(1-chloro-7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (2.00 g) as a yellow oil. The assigned structure was confirmed by proton magnetic spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.29 (3H, t); 1.65 (3H, d); 3.47 (3H, s); 4.27 (2H, q); 4.75 (1H, q); 6.47 (1H, s) 6.85-7.20 (6H, m); 7.30 (1H, d).

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-a7bc75368ebb43ab8d622e1a4fb51688
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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