Diethyl Ether → 3,4-Dimethoxy-1-methylquinolin-2(1H)-one

HRID 1612762Notes

Reaction equation

HRID 1612762 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4](=NO)[C:3]1=[O:15].[N+](=[CH2:18])=[N-].C[CH2:20][O:21]CC>C(Cl)Cl.CO>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:18])=[C:4]([O:21][CH3:20])[C:3]1=[O:15]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 178481576HCID 178481576, compound2×

Product 1

HCID 143352303,4-Dimethoxy-1-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-methyl-3,4-dihydroxy-2(1H)-quinolinone (0.2 gm, Example 7, obtained from Formula 1.02, see Example 1) in methylene chloride (5 ml) and methanol (5 ml) was treated with a solution of excess diazomethane in ether. The resulting solution was evaporated and the residue was chromatographed on silica gel (5 gm). The major product of the reaction was eluted with 1% methanol/methylene chloride and crystallized from ethyl acetate-hexane to give the title compound. That the expected product was obtained was confirmed by the spectral data: MS: m/e 219 (M.+ +1); NMR(CDCl3): δ3.71 (s, 3H, CH3 --N), 3.94 (s, 3H, OCH3), 4.22 (s, 3H, OCH3) ppm.

Workup

  1. customThe resulting solution was evaporated
  2. customthe residue was chromatographed on silica gel (5 gm)
  3. washThe major product of the reaction was eluted with 1% methanol/methylene chloride
  4. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f1660ef5860e4878b12379f86d6721d1
Source dataset
uspto-grants-1993_03
Patent number
US05190956

Reaction notes

Loading…