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

HRID 2069031Notes

Reaction equation

HRID 2069031 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.[H][H]>CO.[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 2

HCID 595473662-(3-Nitropyridin-4-yl)ethanolHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(3-nitropyridin-4-yl)ethanol (24) (WO 2006136562) (2.00 g, 11.89 mmol) in MeOH (150 mL) was passed through a Thales H-cube (2.0 mL·min−1, 30° C., 30 bar, Pd/C Cat-Cart, 55 mm, controlled mode). Analysis by LC-MS showed a significant amount of starting material was still present and the solution was passed through the H-cube twice more (2.0 mL·min−1, full hydrogen mode, RT, and 2.0 mL·min−1, full hydrogen mode, 40° C.). Evaporation of the volatiles gave the title compound (25) as a purple oil (1.30 g, 81%): m/z 139 (M+H)+ (ES+).

Workup

  1. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-e0b9021797f74caca4a19d2ac18a2997
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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