Sodium hydride → 8-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one

HRID 1398338Notes

Reaction equation

HRID 1398338 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])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4](F)[CH:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 867103364-(4-chloro-2-fluorophenyl)-N,2-dimethylnicotinamide

Product 1

HCID 867103378-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-oneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-2-fluorophenyl)-N,2-dimethylnicotinamide (40 mg, 0.144 mmol) in THF (3 mL) cooled to 0° C. was added NaH (10.33 mg, 0.431 mmol) and the reaction mixture was stirred for 4 h. After the reaction completion, the reaction mixture was quenched with ice water and the product was extracted with ethyl acetate (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (30 mg, 0.116 mmol, 81% yield) as an off-white solid. LC/MS, (ESI) m/z 259.2 [(M+H)+, calcd for C14H12ClN2O 259.1]; LC/MS retention time (Method D): tR=0.65 min.

Workup

  1. customAfter the reaction completion, the reaction mixture was quenched with ice water
  2. extractionthe product was extracted with ethyl acetate (20 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cf0928f607c4a80b4da26c5e01871c4
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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