Sodium borohydride → HCID 118075826, compound

HRID 1051568Notes

Reaction equation

HRID 1051568 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[BH4-].[Na+]>[Ni](Cl)Cl.CO>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 118075914HCID 118075914, compound

Product 1

HCID 118075826HCID 118075826, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

A glass, screw-cap vial equipped with a magnetic stir bar was charged with 2-methyl-5-phenoxyquinoline (0.05 g, 0.213 mmol), methanol (1 mL), and nickel(II) chloride (4.96 mg, 0.038 mmol). Sodium borohydride (0.032 g, 0.850 mmol) was added portion-wise over 30 sec at rt. The reaction mixture turned dark purple (almost black), and an exotherm was observed. After 10 min, the reaction mixture was concentrated under a stream of nitrogen. The residue was then treated with 1 N aqueous sodium hydroxide solution (1 mL) and dichloromethane (2-3 mL). The resulting emulsion was filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated to afford rac-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinoline (0.051 g) as a pale yellow syrup. The crude product was carried forward without further purification. MS (ESI, pos. ion) m/z 240 [M+1].

Workup

  1. customA glass, screw-cap vial
  2. customequipped with a magnetic stir bar
  3. concentrationthe reaction mixture was concentrated under a stream of nitrogen
  4. additionThe residue was then treated with 1 N aqueous sodium hydroxide solution (1 mL) and dichloromethane (2-3 mL)
  5. filtrationThe resulting emulsion was filtered through a pad of Celite
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c23bc2598c6943d981de5486a167af06
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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