Lithium hydroxide, monohydrate → 5-(3-Hydroxypyrrolidin-1-yl)picolinamide

HRID 1504604Notes

Reaction equation

HRID 1504604 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=2)[CH2:3]1.[OH:15][Li].O>OO>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([NH2:14])=[O:15])=[N:11][CH:12]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 867300605-(3-Hydroxypyrrolidin-1-yl)picolinonitrile

Product 1

HCID 867300615-(3-Hydroxypyrrolidin-1-yl)picolinamideYield 74.2%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

A mixture of 5-(3-hydroxypyrrolidin-1-yl)picolinonitrile (2.7 g, 14.3 mmol) in H2O2 (30 mL) was added LiOH.H2O (1.8 g, 42.9 mmol) and the mixture was stirred at rt for 16 h. The precipitate was collected by filtration and the cake was washed with water (20 mL) to give the desired product (2.2 g, 74%) as a yellow solid. [LCMS: RtA=1.05 min, m/z 208.2 [M+H]+].

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washthe cake was washed with water (20 mL)

Sources & evidence

ORD record
ord-d2300eb3f2d74e0f85f87b0887dac80b
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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