1,2,3,4-Tetrahydroisoquinoline → HCID 47100857, compound

HRID 1428836Notes

Reaction equation

HRID 1428836 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][NH:13]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:13]1[CH2:14][CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 47100857HCID 47100857, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,4-dichloronitrobenzene (1.0 g, 5.2 mmol), 1,2,3,4-tetrahydroisoquinoline (0.97 g, 7.3 mmol), K2CO3 (3.6 g, 26 mmol), and DMSO (20 mL) was heated to 80° C. for 16 h with stirring. The mixture was allowed to cool to rt, and was then poured over ice. The resulting precipitate was collected by filtration and dried to provide the titled compound (1.5 g, 98%). MS (ESI): mass calcd. for C15H13ClN2O2, 288.7; m/z found, 289.1 [M+H]+.

Workup

  1. temperatureto cool to rt
  2. additionwas then poured over ice
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-9aa5bc5bce4246a68ccf5e5281898fbe
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…