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

HRID 1398427Notes

Reaction equation

HRID 1398427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=2)=[C:4](F)[CH:3]=1.[H-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 867104134-(4-chloro-2-fluorophenyl)-N,6-dimethylnicotinamide

Product 1

HCID 867104148-chloro-2,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-oneYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-2-fluorophenyl)-N,6-dimethylnicotinamide (520 mg, 1.86 mmol) in tetrahydrofuran (20 mL) at 0° C. was added NaH (224 mg, 5.60 mmol). The reaction mixture was brought to room temperature gradually and stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to afford 8-chloro-2,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (480 mg, 1.51 mmol, 81% yield) as a brick-red solid. LC/MS (ESI) m/e 259.0 [(M+H)+, calcd for C14H12ClN2O 259.05]; LC/MS retention time (method C): tR=1.91 min. 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.41 (s, 1H), 8.48 (d, J=8.59 Hz, 1H), 8.23 (s, 1H), 7.69 (d, J=1.98 Hz, 1H), 7.44 (dd, J=8.64, 1.94 Hz, 1H), 3.78 (s, 3H), 2.75 (s, 3H).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98931a035b814466b82e57b21ad6f322
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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