Water → HCID 86716175, compound

HRID 512152Notes

Reaction equation

COC([C:5]1[CH2:10][C:9]([C:13]2[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=2)([C:11]#[N:12])[CH2:8][CH2:7][C:6]=1[OH:20])=O.[Cl-].[Na+].O>CS(C)=O>[Cl:19][C:16]1[N:15]=[CH:14][C:13]([C:9]2([C:11]#[N:12])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 5-(6-chloro-pyridin-3-yl)-5-cyano-2-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (4.2 g, 14 mmol) in DMSO (15 mL) was added sodium chloride (090 g, 16 mmol) and water (0.77 mL). The reaction mixture was heated at 160° C. for 6 hours. The reaction mixture was then cooled to room temperature and poured into water (50 mL). The aqueous layer was extracted with diethyl ether (3×250 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel to afford 1-(6-chloro-pyridin-3-yl)-4-oxo-cyclohexanecarbonitrile (1.7 g, 52%). 1H NMR (400 MHz, CDCl3) δ ppm 8.59 (s, 1 H), 7.83 (dd, J=8.4, 2.2 Hz, 1 H), 7.44 (d, J=8.5 Hz, 1 H), 2.89-2.98 (m, 2 H), 2.60-2.66 (m, 2 H), 2.48-2.54 (m, 2 H), 2.25-2.33 (m, 2 H).

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionThe aqueous layer was extracted with diethyl ether (3×250 mL)
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-f22bc21178b14e4b9c603c19624e121a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102591B2

Reaction notes

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