Hydrochloric Acid → HCID 54725312, compound

HRID 1797489Notes

Reaction equation

HRID 1797489 reaction equation
C(O[C:4]([C:6]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)=[O:5])C.[CH2:19]([NH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:20]([CH3:23])([CH3:22])[CH3:21].Cl.C(N=C=NCCCN(C)C)C.C(O)C.[O-]CC.[Na+].Cl>CN(C)C=O.O>[CH3:16][O:15][C:14]1[C:13]([O:17][CH3:18])=[CH:12][CH:11]=[C:7]2[C:6]=1[C:4]([OH:5])=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:24]([CH2:19][C:20]([CH3:21])([CH3:22])[CH3:23])[C:8]2=[O:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11482198HCID 11482198, compoundHCID 22176037HCID 22176037, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 54725312HCID 54725312, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(ethoxycarbonyl)-3,4-dimethoxybenzoic acid (4.45 g, 17.5 mmol), ethyl 2-(neopentylamino)acetate (3.47 g, 20 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.83 g, 20 mmol) in N,N-dimethylformamide (50 ml) was stirred at room temperature for 3 h. The reactions mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (50 ml) and 20% sodium ethoxide ethanol solution (34.04 g, 100 mmol) was added thereto. The mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (150 ml) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ethyl 5,6-dimethoxy-4-hydroxy-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (3.21 g, 50.6%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (50 ml)
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9213465fdf34de1865c6f59217e797d
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…