2-(3-Nitropyridin-4-yl)ethanol → 4-Pyridineethanol, 3-amino-

HRID 2067063Notes

Reaction equation

HRID 2067063 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][OH:12])([O-])=O>CO.[H][H].[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 1

HCID 595473662-(3-Nitropyridin-4-yl)ethanol

Product 1

HCID 468355964-Pyridineethanol, 3-amino-Yield 81%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

2-(3-Nitropyridin-4-yl)ethanol (15) (WO 2006136562) (2.00 g, 11.89 mmol) in MeOH (150 mL) was passed through a Thales H-cube at 2.0 mL·min−1 using Pd/C Cat-Cart (55 mm) in controlled mode at 30° C., 30 bar. Analysis by LC-MS showed a significant amount of starting material was still present. The solution was passed through the H-cube a second time at 2.0 mL·min−1 in full hydrogen mode at RT, and again at 2.0 mL·min−1 in full hydrogen mode at 40° C. Evaporation of the volatiles gave 2-(3-Aminopyridin-4-yl)ethanol (16) as a purple oil (1.30 g, 81%): m/z 139 (M+H)+ (ES+).

Workup

  1. customat 30° C.
  2. customat RT
  3. customat 40° C
  4. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-6aa2ab494b594ecd9c23e01fbde86180
Source dataset
uspto-grants-2012_10
Patent number
US08293748B2

Reaction notes

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