Dimethylformamide → HCID 20484881, compound

HRID 647428Notes

Reaction equation

HRID 647428 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[N:11]=[C:12]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>ClCCl>[Cl:9][C:10]1[N:11]=[C:12]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:23][CH:22]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13386235HCID 13386235, compound

Product 1

HCID 20484881HCID 20484881, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-bromopropionate (1.33 g), 4-[N-(3-chloroisoquinolin-1-yl)amino]phenol (1.80 g), anhydrous potassium carbonate (1.01 g) and dimethyl formamide was heated, with stirring, at a temperature of 100° C. for a period of 1 hour. The mixture was cooled and poured into dichloromethane and the resulting mixture was repeatedly washed with water. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography over silica gel (eluant dichloromethane) to give ethyl 2-{4-[N-(3-chloroisoquinolin-1-yl)amino]phenoxy}propionate (1.74 g) as a yellow oil. The assigned structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ ppm); 1.20 (3H, t); 1.50 (3H, d); 4.12 (2H, q); 4.60 (1H, q); 6.60-8.20 (10H, m).

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. washthe resulting mixture was repeatedly washed with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-feaa709b5c2949f79f192f97696a125c
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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