1,2-Dimethoxyethane → 2-(3-Chlorophenyl)quinoline

HRID 539474Notes

Reaction equation

HRID 539474 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 119282-ChloroquinolineHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 156059482-(3-Chlorophenyl)quinolineYield 77.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

2-chloroquinoline (9.25 g, 56.5 mmol), (3-chlorophenyl)boronic acid (9.28 g, 59.4 mmol), Pd(PPh3)4 (1.634 g, 1.413 mmol) were charged into the reaction flask with 300 mL of 1,2-dimethoxyethane. Sodium carbonate (14.98 g, 141 mmol) was dissolved in 50 mL of water and was charged into the reaction flask. The reaction flask was then evacuated and back-filled with nitrogen then was heated to reflux for 20 hours. The organic layer was separated and dried over magnesium sulfate. The organics were filtered and stripped under vacuum. The crude residue was passed through a silica gel column using 5-25% ethyl acetate/hexanes yielding 2-(3-chlorophenyl)quinoline (10.5 g, 77% yield) as a white solid.

Workup

  1. additionwas charged into the reaction flask
  2. customThe reaction flask was then evacuated
  3. additionback-filled with nitrogen
  4. temperaturethen was heated
  5. temperatureto reflux for 20 hours
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe organics were filtered

Sources & evidence

ORD record
ord-d90d8ee1325d4fecbe62b3d53601b59d
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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