Hydrochloric Acid → 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]pyridine Hydrochloride

HRID 612495Notes

Reaction equation

HRID 612495 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:13].[BH4-].[Na+].O.[ClH:23]>CCO>[ClH:23].[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:14]1[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=1)[OH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 195954432-(2,3-Dimethoxyphenyl)-1-(4-pyridinyl)ethanone

Product 1

HCID 195954564-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]pyridine Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 2-(2,3-dimethoxyphenyl)-1-(4-pyridinyl)ethanone (2.4 g, 0.009 mol) in EtOH (25 ml) was added, portionwise, NaBH4 (0.005 mol). The reaction was stirred at ambient temperature for 2 h, and then it was poured into water. The aqueous solution was extracted with EtOAc, and the extract was washed (water), dried (magnesium sulfate) and concentrated to afford an oil. The oil was triturated with Et2O and 1.9 g of a white solid resulted. The solid was dissolved in EtOH and ethereal HCl was added to precipitate a white hydrochloride salt. The salt was recrystallized twice from EtOH to afford the alcohol as a white solid mp 204-206° C.

Workup

  1. extractionThe aqueous solution was extracted with EtOAc
  2. washthe extract was washed (water)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto afford an oil
  6. customThe oil was triturated with Et2O and 1.9 g of a white solid
  7. customresulted
  8. customto precipitate a white hydrochloride salt
  9. customThe salt was recrystallized twice from EtOH

Sources & evidence

ORD record
ord-f18efd86e0584e2abd56d4231be44f8a
Source dataset
uspto-grants-1999_12
Patent number
US06004982

Reaction notes

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