Water → 2-(Benzo[2,1,3]oxadiazol-5-yloxy)-nicotinic acid ethyl ester

HRID 1297585Notes

Reaction equation

[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=12.[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1Cl)[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[O:10][C:8]1[CH:7]=[CH:6][C:5]2=[N:1][O:2][N:3]=[C:4]2[CH:9]=1)[CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of benzo[2,1,3]oxadiazol-5-ol (4.0 g), 2-chloro-nicotinic acid ethyl ester (5.5 g), and cesium carbonate (21.1 g) in dimethylformamide (125 mL) was stirred rapidly and heated to 90° C. for 7 days. The reaction was then cooled to ambient temperature and poured into water (600 mL). The aqueous was extracted with ethyl acetate (5×150 mL). The combined organics were washed with saturated sodium bicarbonate (500 mL), water (2×500 mL), and brine (500 mL), then dried over sodium sulfate and concentrated to give a pale solid which was recrystalized from diethyl ether/pentane to give the title compound (2.2 g)

Workup

temperatureThe reaction was then cooled to ambient temperature
extractionThe aqueous was extracted with ethyl acetate (5×150 mL)
washThe combined organics were washed with saturated sodium bicarbonate (500 mL), water (2×500 mL), and brine (500 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated
customto give a pale solid which
customwas recrystalized from diethyl ether/pentane

Sources & evidence

ORD record: ord-c4d2da7cd3dd4fcd8b2d63128a71ac44
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250518B2

Reaction notes

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