Sodium Carbonate → HCID 13769199, compound

HRID 2232528Notes

Reaction equation

HRID 2232528 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([OH:17])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([N:20]([CH2:25][CH3:26])[C:21](=[O:24])[CH2:22]Cl)[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>CC(=O)CC>[CH2:18]([N:20]([CH2:25][CH3:26])[C:21](=[O:24])[CH2:22][O:17][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 178517442HCID 178517442, compound

Product 1

HCID 13769199HCID 13769199, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure is as in Example 47, starting with 3-phenyl-1-isoquinolinol (5.1 g), N,N-diethylchloroacetamide (3.8 g), sodium carbonate (4.8 g) and cuprous iodide (1.15 g) in 2-butanone (100 cc). After 2 chromatographic separations on silica gel with chloroform as eluant and crystallization of the product in petroleum ether, N,N-diethyl-(3-phenyl-1-isoquinolyl)oxyacetamide (0.5 g), m.p. 102° C., is obtained.

Workup

  1. customAfter 2 chromatographic separations on silica gel with chloroform as eluant and crystallization of the product in petroleum ether

Sources & evidence

ORD record
ord-7b6eb0838d3549d98ebadc0d7ee3dbfb
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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