Sodium hydride → HCID 20356988, compound

HRID 259239Notes

Reaction equation

HRID 259239 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:19])[C:7]([C:14]([O:16]CC)=[O:15])=[CH:8][NH:9]3)=[CH:4][C:3]=2[O:2]1.[H-].[Na+].ClC(Cl)(Cl)S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O>CN(C)C=O>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:19])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 842571,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 8-hydroxy-, ethyl esterHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonate

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, ethyl ester (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 is maintained at 80°-90° for an additional 2 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 4.

Workup

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

Sources & evidence

ORD record
ord-6d3a9ca4441c434b99b59ad6ec27c6e5
Source dataset
uspto-grants-1977_07
Patent number
US04036962

Reaction notes

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