Sodium hydride → HCID 20356988, compound

HRID 2083573Notes

Reaction equation

HRID 2083573 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][NH:9]3)=[CH:4][C:3]=2[O:2]1.[H-].[Na+].ClC(Cl)(Cl)S(O[CH2:26][C:27]([F:30])([F:29])[F:28])(=O)=O>CN(C)C=O>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 1522615,8-Dihydro-8-oxo-2H-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid

Product 1

HCID 20356988HCID 20356988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.6 (0.06 mole) of 6,7-methylenedioxy-4(1H)-quinolone-3-carboxylic acid (J. Med. Chem. 11, 160 (1968)) and 1.5 g. (0.062 mole) of sodium hydride powder in 250 ml. of dimethyl formamide was heated with stirring for 0.5 hour at 80°-90° C. 2,2,2-Trifluoroethyl trichloromethanesulfonate (17.5 g. 0.62 mole) was then added dropwise. The temperature was maintained at 80°-90° for an additional two hours. The cooled mixture was poured into ice water and the solid product was isolated by filtration. It was recrystallized from ethanol. This product was identical to that obtained from Example 1.

Workup

  1. temperatureThe temperature was maintained at 80°-90° for an additional two hours
  2. customthe solid product was isolated by filtration
  3. customIt was recrystallized from ethanol
  4. customthat obtained from Example 1

Sources & evidence

ORD record
ord-847fb38641a1462c9dcd648e008e227e
Source dataset
uspto-grants-1978_04
Patent number
US04086236

Reaction notes

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