Potassium Carbonate → 5-(3-Hydroxypyrrolidin-1-yl)picolinonitrile

HRID 1504603Notes

Reaction equation

HRID 1504603 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.Cl.[NH:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:16][CH:13]1[CH2:14][CH2:15][N:11]([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27694083-Hydroxypyrrolidine hydrochlorideHCID 38339425-Chloro-2-cyanopyridine

Product 1

HCID 867300605-(3-Hydroxypyrrolidin-1-yl)picolinonitrileYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloropicolinonitrile (2 g, 14.4 mmol), pyrrolidin-3-ol hydrochloride (2 g, 25.9 mmol) and K2CO3 (4 g, 28.9 mmol) in DMF (15 mL) was stirred at 140□ for 16 h. The organic solvent was removed under vacuum and the residue was taken into DCM (200 mL). Solid was removed by filtration and the filtrate was concentrated to give crude product (2.0 g yield 73%) as a yellow solid. [LCMS: RtA=1.19 min, m/z 190.2 [M+H]+].

Workup

  1. customThe organic solvent was removed under vacuum
  2. customSolid was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6aef93b6768d4374969efb501e788bcd
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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