Water → 6-(Benzyloxy)-2-chloroquinoline

HRID 1869794Notes

Reaction equation

HRID 1869794 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([Cl:1])[CH:11]=[CH:10]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 221325772-Chloroquinolin-6-ol

Product 1

HCID 112194246-(Benzyloxy)-2-chloroquinolineYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-6-quinolinol 11 (5.45 g) in DMF (100 ml) is added, at 0° C., cesium carbonate (11.9 g). After 15 minutes at 0° C., benzyl bromide (4 ml) is added and the reaction is stirred for 12 h at room temperature. Water (100 ml) is then added and the solid obtained is filtered and washed with pentane. No further purification is needed. 6-(benzyloxy)-2-chloroquinoline 12 is obtained as a powder.

Workup

  1. customthe solid obtained
  2. filtrationis filtered
  3. washwashed with pentane
  4. customNo further purification

Sources & evidence

ORD record
ord-62b244f4b80f4a1daa7cdd6841da2fdf
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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