Water → Ethyl 2-chloroquinoline-7-carboxylate

HRID 537189Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[N+:18]2[O-])=[CH:13][CH:12]=1)=[O:10])[CH3:7].O.[OH-].[K+]>ClCCl>[Cl:3][C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])=[CH:12][CH:13]=2)[N:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Phosphorus oxychloride (1.94 mL, 20.7 mmol) was added to a solution of 7-(ethoxycarbonyl)quinoline 1-oxide (450 mg, 2.07 mmol) in dichloromethane (15 mL). The reaction was heated to 50° C. for 3 hours. The reaction was then cooled to room temperature and was slowly poured into 200 mL of water, with stirring. The mixture was allowed to stir for 1 hour and was then neutralized with 1 N aqueous potassium hydroxide. The mixture was extracted with dichloromethane (3×). The extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by column chromatography (0-20% ethyl acetate/heptanes) gave the title compound (254 mg, 52%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.70-8.79 (m, 1H), 8.13-8.18 (m, 2H), 7.87 (d, J=8.39 Hz, 1H), 7.47 (d, J=8.58 Hz, 1H), 4.44 (q, J=7.02 Hz, 2H), 1.43 (t, J=7.12 Hz, 3H).

Workup

temperatureThe reaction was then cooled to room temperature
stirringto stir for 1 hour
extractionThe mixture was extracted with dichloromethane (3×)
washThe extracts were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (0-20% ethyl acetate/heptanes)

Sources & evidence

ORD record: ord-cbdfaf1454ac4e90bccbd1fbecfcb20e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859773B2

Reaction notes

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