Sodium hydride → 8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398290Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]([NH:18][CH3:19])=[O:17])=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6](F)[CH:5]=1>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:15](=[CH:14][N:13]=[CH:12][CH:11]=3)[C:16](=[O:17])[N:18]([CH3:19])[C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (80 mg, 3.32 mmol) was taken in THF (1 mL) and cooled to 0° C. To the suspension, 4-(4-chloro-2-fluorophenyl)-N-methylnicotinamide (440 mg, 1.66 mmol) in THF (1 mL) was added dropwise and the temperature was maintained at 0° C. for 30 min. The reaction mixture was then warmed to room temperature and stirred for 2 h. The reaction mixture was quenched with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (1×5 mL) dried (Na2SO4) and concentrated under reduced pressure to afford 8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (440 mg, 1.798 mmol) as a light brown oil. LC/MS (ESI) m/e 245.1 [(M+H)+, calcd for C13H10ClN2O 245.1]; LC/MS retention time (method C): tR=1.79 min.

Workup

temperaturethe temperature was maintained at 0° C. for 30 min
temperatureThe reaction mixture was then warmed to room temperature
customThe reaction mixture was quenched with ice
extractionextracted with ethyl acetate (3×5 mL)
washThe combined organic layers were washed with brine (1×5 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2e8f844c6fb34f1e8e06a4e7fe2d0855
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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