Sodium hydride → HCID 21931711, compound

HRID 1243984Notes

Reaction equation

HRID 1243984 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2.[S:16](Cl)([CH3:19])(=[O:18])=[O:17]>CN(C=O)C>[CH3:19][S:16]([N:11]1[C:12]2[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:14][CH:13]=2)[CH2:8][CH2:9][C:10]1=[O:15])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 21931711HCID 21931711, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flame dried round bottom flask equipped with a nitrogen cap was placed 87 mg (2.17 mmol) of 60% sodium hydride in mineral oil and 15 ml of dimethylformaminde (DMF). The mixture was cooled to 0° C. and was treated with 350 mg (1.97 mmol) of 6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline (Preparation 2) in the minimum amount of DMF. The reaction mixture was stirred for 0.5 hours at 0° C. and was then treated with 226 mg (1.97 mmol) mesyl chloride. The mixture was slowly allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was quenched by the addition of 30 ml of saturated aqueous sodium bicarbonate solution and the mixture was extracted with methylene chloride (3×30 ml). The combined organics were washed with brine, dried over sodium sulfate and evaporated in vacuo. The crude oil was purified by silica gel chromatography eluting with 1/1 ethyl acetate/hexane to afford a light yellow oil in 35% yield (177 mg). Mass spectrum APCI m/e 256 (p+1).

Workup

  1. customTo a flame dried round bottom flask
  2. customequipped with a nitrogen
  3. customcap
  4. temperatureto warm to room temperature
  5. stirringstirred for 16 hours
  6. customThe reaction mixture was quenched by the addition of 30 ml of saturated aqueous sodium bicarbonate solution
  7. extractionthe mixture was extracted with methylene chloride (3×30 ml)
  8. washThe combined organics were washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customThe crude oil was purified by silica gel chromatography
  12. washeluting with 1/1 ethyl acetate/hexane
  13. customto afford a light yellow oil in 35% yield (177 mg)

Sources & evidence

ORD record
ord-8ada481145894041bdccb40c48d1b0f3
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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