Water → 2-Methyl-3-nitro-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridine

HRID 390312Notes

Reaction equation

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[N:3]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].O>ClCCl>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH:12]2[CH2:16][CH2:15][N:14]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:13]2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methyl-3-nitro-6-(pyrrolidin-3-yloxy)pyridine (1.3 g) was dissolved in dichloromethane (20 ml) and triethylamine (1.57 ml) was added. The solution was cooled to 0° C. and a solution of propionyl chloride (574 mg) in dichloromethane (5 ml) was added dropwise over 5 min. The reaction mixture was allowed to come to room temperature and was stirred for another 5 min. Water (10 ml) was added. After stirring for 3 min, the phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane/methanol=98/2). Yield: 950 mg (64.9%, pale yellow oil).

Workup

customto come to room temperature
stirringAfter stirring for 3 min
customthe phases were separated
extractionthe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic layers were dried (sodium sulfate)
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography (silica, dichloromethane/methanol=98/2)

Sources & evidence

ORD record: ord-7ad4eb3fc29f476aa706b8a2ed8f1dd3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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