Acetic Acid → 2-hydroxy-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile

HRID 1771518Notes

Reaction equation

N1(C[C:8](O)=[O:9])CCCCC1.C(O)(=O)C.N1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:21]([CH2:23][C:24]([NH2:26])=[O:25])#[N:22]>O>[O:25]=[C:24]1[NH:26][C:18]2[CH2:19][CH2:20][O:9][CH2:8][C:17]=2[CH:16]=[C:23]1[C:21]#[N:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Then, an aqueous piperidine—acetic acid solution prepared by dissolving acetic acid (1.5 mL) in water (3.5 mL) and adding piperidine (2.6 ml) thereto, and 2-cyanoacetamide (4.62 g, 54.9 mmol) were added to the above-mentioned aqueous solution A, and the mixture was stirred with heating under reflux for 4 hr. To the mixture was added acetic acid (3.6 mL) and, after cooling 0° C., the precipitated solid was collected by filtration to give 2-oxo-1,5,7,8-tetrahydro-2H-pyrano[4,3-b]pyridine-3-carbonitrile (1.72 g, 20%) as a white solid.

Workup

temperaturewith heating
temperatureunder reflux for 4 hr
filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-cfe2eb3a153b4f62aec037d99243115b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249135B2

Reaction notes

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