Water → 8-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylquinoline

HRID 342612Notes

Reaction equation

HRID 342612 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2.[Cl:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([Cl:31])[C:21]=1[CH2:22]Br.O>CN(C=O)C>[Cl:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([Cl:31])[C:21]=1[CH2:22][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132242-Methyl-8-hydroxyquinolineHCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Product 1

HCID 104989148-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (10.8 g, 33.3 mmol) was added at room temperature to 8-hydroxy-2-methylquinoline (5 g, 33.3 mmol) in DMF (65 ml). After 30 min, 2,6-dichloro-3-nitrobenzyl bromide (13 g, 45.6 mmol) was added. After 18 h, H2O was added and the precipitate was filtered off with suction and washed with EA (50 ml), the title compound being obtained as an amorphous substance.

Workup

  1. waitAfter 18 h
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with EA (50 ml)

Sources & evidence

ORD record
ord-a8be8013f9e0459f8433499fad2dcbee
Source dataset
uspto-grants-1999_01
Patent number
US05859025

Reaction notes

Loading…