Sodium Carbonate → HCID 13769200, compound

HRID 2232529Notes

Reaction equation

HRID 2232529 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[N:8]=2)[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[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 178515320HCID 178515320, compound

Product 1

HCID 13769200HCID 13769200, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure is as in Example 47, starting with 1-phenyl-3-isoquinolinol (4.4 g), N,N-diethyl-2-chloroacetamide (3.3 g), sodium carbonate (4.25 g) and cuprous iodide (1 g) in 2-butanone (90 cc). After chromatography on silica gel with a chloroform/methanol (98:2 by volume) mixture as eluant and crystallization of the product in isopropyl ether, N,N-diethyl-(1-phenyl-3-isoquinolyl)oxyacetamide (2.6 g), m.p. 105° C., is obtained.

Workup

  1. customAfter chromatography on silica gel with a chloroform/methanol (98:2 by volume) mixture as eluant and crystallization of the product in isopropyl ether

Sources & evidence

ORD record
ord-b84ed257ec924f97a53c6ab87f5241e5
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

Loading…