Hydrochloric Acid → 2-(1-Pyrrolidinyl)-3-pyridinol

Reaction equation

Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>>[N:9]1([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 230702-Bromo-3-pyridinol

HCID 31268Pyrrolidine

Product 1

HCID 900023802-(1-Pyrrolidinyl)-3-pyridinolYield 41.3%

Procedure

2-bromopyridin-3-ol (200 mg, 1.15 mmol) and pyrrolidine (184 mg, 2.58 mmol) were added in a reaction tube, followed by reacting in microwave at 120° C. for 20 minutes. The reaction mixture was added with 1 M HCl solution to neutralized, and extracted with ethyl acetate and dichloromethane. The obtained organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 2-(pyrrolidin-1-yl)pyridin-3-ol (78 mg, 41%).

Workup

extractionextracted with ethyl acetate and dichloromethane
dry with materialThe obtained organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate was purified by column chromatography

Sources & evidence

ORD record: ord-48275c11308c4f8f9f29ea0f02a7e2d8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447083B2

Reaction notes

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