HCID 20484885, compound → ethyl 2-[4-[N-(7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate

HRID 647433Notes

Reaction equation

HRID 647433 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[CH:5]=[C:4]([N:13]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH3:14])[N:3]=1>C(O)(=O)C.[Zn]>[F:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 20484885HCID 20484885, compound

Product 1

HCID 20484904ethyl 2-[4-[N-(7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionateYield 60.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (4×1.63 g) was added portionwise over a 2 hr period to a stirred solution of ethyl 2-{4-[N-(1-chloro-7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.00 g) in acetic acid (50 ml). The mixture was filtered and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water. The organic extract was washed successively with, aqueous sodium bicarbonate solution, water, aqueous ethylenediaminetetraacetic acid solution (5%) and water, then dried (MgSO4) and evaporated to give a green oil. Purification by column chromatography over silica gel (eluant dichloromethane) gave ethyl 2-[4-[N-(7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.55 g) as a greenish oil. The assigned structure was confirmed by proton magnetic spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.28 (3H, t); 1.64 (3H, d); 3.48 (3H, s); 4.25 (2H, q); 4.74 (1H, q); 6.62 (1H; s); 6.87-7.37 (7H, m); 8.85 (1H, s).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with acetic acid
  3. customAfter the filtrate was evaporated the residue
  4. customwas partitioned between methylene chloride and water
  5. extractionThe organic extract
  6. washwas washed successively with, aqueous sodium bicarbonate solution, water, aqueous ethylenediaminetetraacetic acid solution (5%) and water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a green oil
  10. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-3efbcf8ab70e4e279937e3c865d54ac1
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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