Ammonium Chloride → HCID 67300903, compound

HRID 1015425Notes

Reaction equation

HRID 1015425 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][CH:22]=[N:23]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH2:20][CH2:21][CH2:22][NH:23]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67301095HCID 67301095, compound

Product 1

HCID 67300903HCID 67300903, compoundYield 40.1%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[5-(naphthalen-1-yloxy)-pentyloxy]-quinoline (0.83 g, 2.32 mmol) in 10 mL methanol and 1 mL THF was added sodium borohydride (0.35 g, 9.29 mmol) and nickel (II) chloride hexahydrate (0.28 g, 1.16 mmol). The reaction mixture was stirred overnight at room temperature and then 20 mL saturated aqueous ammonium chloride solution was added. The solution was extracted with ethyl acetate (3×20 mL), and the combined organic phases were washed with brine, dried over MgSO4, and concentrated to give a white solid. The crude product was purified by silica gel chromatography to give 5-[5-(naphthalen-1-yloxy)-pentyloxy]-1,2,3,4-tetrahydro-quinoline (335 mg, 0.93 mmol, 40%) as a white solid.

Workup

  1. extractionThe solution was extracted with ethyl acetate (3×20 mL)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-141413edab5a4c11822710c84cc26728
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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