Diethyl Sulfate → HCID 20248486, compound

HRID 2418242Notes

Reaction equation

HRID 2418242 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[OH:20].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:31][CH3:32])(=O)=O>CS(C)=O>[CH2:31]([O:20][C:3]1[C:4]2=[C:13]3[N:8]([CH:7]([CH3:19])[CH2:6][CH2:5]2)[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11](=[O:15])[C:12]3=[CH:14][C:2]=1[F:1])[CH3:32]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 20248484HCID 20248484, compound

Product 1

HCID 20248486HCID 20248486, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1.0 g of 6,7-dihydro-9-fluoro-8-hydroxy-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 1.4 g of potassium carbonate and 2.0 ml of diethyl sulfate in 15 ml of dimethyl sulfoxide was heated at its reflux temperature for sixteen hours. The solution was then evaporated to dryness by heating on a steam bath under a stream of nitrogen. Fifty ml of 1% aqueous sodium hydroxide solution was added to the resulting residue. The mixture was heated on a steam bath for one hour, acidified with concentrated hydrocloric acid and cooled. The solid was separated by filtration and recrystallized from aqueous ethanol to provide 6,7-dihydro-8-ethoxy-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 208°-210° C. (dec.). Analysis: Calculated for C16H16FNO4 : %C, 63.0; %H, 5.3; %N, 4.6; Found: %C, 62.9; %H, 5.3; %N, 4.6.

Workup

  1. temperaturereflux temperature for sixteen hours
  2. customThe solution was then evaporated to dryness
  3. temperatureby heating on a steam bath under a stream of nitrogen
  4. additionFifty ml of 1% aqueous sodium hydroxide solution was added to the resulting residue
  5. temperatureThe mixture was heated on a steam bath for one hour
  6. temperaturecooled
  7. customThe solid was separated by filtration
  8. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3b603228829f466fa498a0b51332ecac
Source dataset
uspto-grants-1984_09
Patent number
US04472407

Reaction notes

Loading…