Hydrochloric Acid → 2-Amino-1-(pyridin-3-yl)ethan-1-ol

HRID 1693406Notes

Reaction equation

HRID 1693406 reaction equation
[O:1]=[C:2]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][N:4]1C(=O)C2C(=CC=CC=2)C1=O.[BH4-].[Na+].Cl>C(O)(C)C>[NH2:4][CH2:3][CH:2]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 534035462-(2-Oxo-2-(pyridin-3-YL)ethyl)isoindoline-1,3-dione

Product 1

HCID 37105942-Amino-1-(pyridin-3-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of crude 2-(2-oxo-2-pyridin-3-ylethyl)isoindole-1,3-dione (Preparation 97, 5.0 g, ˜19.0 mmol) in aqueous isopropanol (210 ml, water/IPA: 1/6) was added sodium borohydride (10.2 g, 270 mmol) in 2 portions. The mixture was stirred at rt for 12 h before being carefully acidified (pH 2) with dilute hydrochloric acid (1M). After removal of the solvent the residue was taken up in distillated water (100 mL) and passed down a column filled with ion-exchange resin (Amberlite IR 120, H+-form, 300 g, eluent: 500 mL water then IL of 2 M aqueous ammonia solution). Concentration of the alkaline fractions gave the title compound as a yellow oil. δH (d6 DMSO): 2.74, 2.85 (2H, 2m), 4.66 (1H, m), 5.15 (3H, br s), 7.36 (1H, dd), 7.75 (1H, m), 8.46 (1H, m), 8.56 (1H, m); m/z (ES+)=139.11 [M+H]+; RT=0.21 min.

Workup

  1. customAfter removal of the solvent the residue
  2. additionfilled with ion-exchange resin (Amberlite IR 120, H+-form, 300 g, eluent

Sources & evidence

ORD record
ord-0073c5c3eacc4c169355463718bfa0fd
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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