Sodium Methoxide → 8-chloro-4-methoxy-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398397Notes

Reaction equation

HRID 1398397 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:7]2=1.[CH3:19][O-:20].[Na+]>CO.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:7]2[C:6]3[C:11](=[C:2]([O:20][CH3:19])[N:3]=[CH:4][CH:5]=3)[C:10](=[O:12])[N:9]([CH3:13])[C:8]=2[CH:14]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 867103844,8-dichloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one

Product 1

HCID 867103858-chloro-4-methoxy-6-methylbenzo[c][2,7]naphthyridin-5(6H)-oneYield 38.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4,8-dichloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (1.0 g, 3.58 mmol) in MeOH (1 mL) was added sodium methoxide (0.806 mL, 3.58 mmol). The resultant mixture was heated in a microwave at 80° C. for 25 min. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated, dried over sodium sulphate and evaporated to dryness to afford 8-chloro-4-methoxy-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (0.4 g, 1.391 mmol, 39% crude yield) as a brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 274.8 [(M+H)+, calcd for C14H12ClN2O2, 275.0]; LC/MS retention time (method C): tR=2.06 min.

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9ed7a0865bd147eb801fc06a5adcb293
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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