Methanol → (7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

HRID 657057Notes

Reaction equation

HRID 657057 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=C)=[CH:4][CH:3]=1.C(Cl)Cl.CSC.C[OH:23]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[O:23])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 688179827-Fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone

Product 1

HCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehydeYield 82%

Conditions

Temperature
-70 °C

Procedure

A solution of 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone (5.0 g, 0.025 mmol) in 3:1 CH2Cl2:MeOH (500 mL) was cooled to −70° and 03 was bubbled through the solution for 20 min. Dimethyl sulfide (19 mL, 0.25 mol) were added and the reaction was stirred for 90 min at −70° C., then allowed to warm to room temperature overnight. The solvents were removed under reduced pressure yielding a thick orange oil. Purification by column chromatography on silica gel (1% to 100% hexane:ethyl acetate gradient) yielded a dark yellow solid (4.2 g, 82%).

Workup

  1. custom03 was bubbled through the solution for 20 min
  2. temperatureto warm to room temperature overnight
  3. customThe solvents were removed under reduced pressure
  4. customyielding a thick orange oil
  5. customPurification by column chromatography on silica gel (1% to 100% hexane:ethyl acetate gradient)

Sources & evidence

ORD record
ord-12f5e94cef4c4b69801d9a400175c1b7
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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