Sodium borohydride → 7-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422569Notes

Reaction equation

HRID 2422569 reaction equation
[O:1]=[CH:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 597749037-(2-Oxoethyl)-4-phenylquinoline-2-carbonitrile

Product 1

HCID 597748837-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(2-oxoethyl)-4-phenylquinoline-2-carbonitrile (1.5 g, 5.5 mmol) in THF (30 mL) and MeOH (10 mL) was added portionwise at 0° C. sodium borohydride (320 mg, 8.4 mmol). The mixture was stirred overnight at rt. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 concentrated under reduced pressure and purified on silica gel (eluting with ethyl acetate/hexanes, 1:1) to give the title compound. MS (+ESI): 275 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica gel (eluting with ethyl acetate/hexanes, 1:1)

Sources & evidence

ORD record
ord-bac19b0c6d7140f38ba4ea91741ed8e0
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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