Nitrogen → 7-chloroquinoline

HRID 513807Notes

Reaction equation

HRID 513807 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.N#N.CN(CCN(C)C)C.[BH4-].[Na+]>C1COCC1.[Cl-].[Na+].O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 68664,7-DichloroquinolineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 4311764Sodium borohydride

Product 1

HCID 5219637-chloroquinolineYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4,7 Dichloroquinoline (10 g, 50 mmol) in THF (100 ml) was degassed with N2 for 5 min. PdCl2dppf (1.2 g, 2 mmol), TMEDA (9.97 g, 86 mmol), and NaBH4 (3.24 g, 86 mmol) were added and the mixture was stirred at room temperature for 5 h. Brine (20 ml) was added dropwise and the solvent was removed in vacuo. The residue dissolved in EtOAc (200 ml), dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAC (4:1-1:1 gradient) as the eluent to give the title compound (5.4 g, 65%).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue dissolved in EtOAc (200 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography with heptane/EtOAC (4:1-1:1 gradient) as the eluent

Sources & evidence

ORD record
ord-148e0c9b51c14c9f8e4c3a9e44a4a6a3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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