Methyl iodide → HCID 21931841, compound

HRID 1244053Notes

Reaction equation

HRID 1244053 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[N:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12](=[O:16])[NH:13]2)=[CH:8][C:7]=1[O:17][CH3:18].[CH3:19]C(C)([O-])C.[K+].CI>CN(C=O)C.O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[N:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12](=[O:16])[N:13]2[CH3:19])=[CH:8][C:7]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 21931736HCID 21931736, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21931841HCID 21931841, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.1 g (0.4 mmol) 7-[1,3]dioxolan-2-yl-6-methoxy-3,4-dihydro-1H-[1,8]naphthyridin-2-one in 1 ml of DMF cooled to 5° C. was added 0.5 ml (0.5 mmol) of potassium t-butoxide (1M solution in THF). The reaction mixture was stirred fo 30 minutes. To this mixture was added 0.06 ml (1 mmol) of methyl iodide and the reaction stirred at ambient temperature for 2 hours. The reaction mixture was diluted with 5 ml of water and extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated to yield intermediate 7-[1,3]dioxolan-2-yl-6-methoxy-1-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one as a dark oil. Mass spectrum: m/e=205.1 (p+1). This material was dissolved in 5 ml of acetone containing 0.1 g of para-toluenesulfonic acid and refluxed for 2 hours. The reaction mixture was evaporated and the residue triturated with saturated NaHCO3. This mixture was extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated and the residue chromatographed on silica using 3:1 chloroform/ethyl acetate as the elutant. Appropriate fractions were combined to yield 12 mg of 3-methoxy-8-methyl-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbaldehyde as an oil. Mass spectrum: m/e=221.1 (p+1). 1H NMR (CDCl3) δ 10.1 (s, 1H), 7.25 (s, 1H), 3.95 (s, 3H), 3.50 (s, 3H), 3.0 (m, 2H), 2.90 (m, 2H).

Workup

  1. stirringthe reaction stirred at ambient temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fd87be97316f42a3a5427560b94ee0a7
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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