Sodium Chloride → 6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one
Reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2.[CH3:14]C(C)([O-])C.[K+].CI.[Na+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:14])[C:8](=[O:13])[CH2:7][CH2:6]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.2 g (6.7 mmol) 6-methoxy-3,4-dihydro-1H-[1,5]naphthyridin-2-one in 15 ml of DMF was cooled to 5° C. and to this solution was slowly added 6.7 ml (6.7 mmol) of potassium t-butoxide (1M solution in THF). The mixture was stirred for 10 minutes followed by addition of 0.46 ml (7.4 mmol) methyl iodide. After addition was complete, the reaction mixture was stirred for 1 hour at 5° C. The reaction mixture was poured into saturated NaCl. The mixture was extracted with ethyl acetate. The ethyl acetate extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined and evaporated to yield 0.83 g of 6-methoxy-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one. TLC Rf=0.6 (1:10 ethyl acetate/chloroform). 1H NMR (CDCl3) δ 7.2 (d, 1H), 6.6 (d, 1H), 3.9 (s, 3H), 3.3 (s, 3H), 3.0 (m, 2H), 2.7 (m, 2H). Mass Spectrum: m/e 193.2 (p+1).
Workup
- additionAfter addition
- stirringthe reaction mixture was stirred for 1 hour at 5° C
- extractionThe mixture was extracted with ethyl acetate
- dry with materialThe ethyl acetate extracts were dried (Na2SO4)
- customevaporated
- customThe residue was chromatographed on silica using 5:1 chloroform/ethyl acetate as the elutant
- customevaporated
Sources & evidence
- ORD record
- ord-4f2957189031418a90e3e9f7a5368829
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119207B2
Reaction notes
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