N-bromobutanimide → Ethyl 6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylate

HRID 598241Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=1[C:13]([F:16])([F:15])[F:14])=[O:5])[CH3:2].BrN1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]=1[C:13]([F:16])([F:14])[F:15])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 1,4,5,6-tetrahydro-6-oxo-2-(trifluoromethyl)-3-pyridinecarboxylic acid ethyl ester (136.15 g, 0.57 mol) in tetrachloromethane (450 mL) was added N-bromosuccinimide (113 g, 0.60 mol). The temperature was slowly raised with stirring to 70° C. and reflux temperature was maintained for 20 h. The mixture was cooled and extracted with water (1000 mL) and dichlormethane (1000 mL). The water phase was extracted twice more with dichloromethane (2×500 mL) and the dichloromethane phases washed with water (2×1000 mL) and dried with MgSO4. Removal of the solvents yielded the title compound (153.4 g), which was used without further purification in the next reaction.

Workup

temperatureThe temperature was slowly raised
temperaturereflux temperature
temperaturewas maintained for 20 h
temperatureThe mixture was cooled
extractionextracted with water (1000 mL) and dichlormethane (1000 mL)
extractionThe water phase was extracted twice more with dichloromethane (2×500 mL)
washthe dichloromethane phases washed with water (2×1000 mL)
dry with materialdried with MgSO4
customRemoval of the solvents

Sources & evidence

ORD record: ord-880abdbce1a849cbb020e481197da9dd
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897621B2

Reaction notes

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