Hydrochloric Acid → 4'-(Hydroxymethyl)-2'-nitrobiphenyl-2-carbonitrile

HRID 1412589Notes

Reaction equation

HRID 1412589 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:17]([O-:19])=[O:18])[CH:4]=1)=[O:2].CO.[BH4-].[Na+].Cl>C1COCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:17]([O-:19])=[O:18])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 866440744'-Formyl-2'-nitrobiphenyl-2-carbonitrile

Product 1

HCID 670092004'-(Hydroxymethyl)-2'-nitrobiphenyl-2-carbonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4′-formyl-2′-nitrobiphenyl-2-carbonitrile (5.15 g), methanol (30 mL) and hydrofuran (30 mL) was gradually added sodium borohydride (0.40 g) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into 1 M hydrochloric acid (20 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow oil (3.62 g, 70%).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5543e5b903b84b3a832c416725cfbf90
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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