Ethanol → HCID 11471099, compound

HRID 2068683Notes

Reaction equation

HRID 2068683 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:16])[C:7]([C:13]([OH:15])=[O:14])=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:21][CH2:22]O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:16])[C:7]([C:13]([O:15][CH2:21][CH3:22])=[O:14])=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24386Thionyl ChlorideHCID 1126045HCID 1126045, compound

Product 1

HCID 11471099HCID 11471099, compound

Procedure

A solution of 7-chloro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.50 g, 2.10 mmol) and SOCl2 (2.0 mL) in EtOH (15.0 mL) was heated to 78° C. for 6 h. After the completion of reaction (TLC monitoring), EtOH was distilled off, added water and extracted with EtOAc (3×70 mL). The combined organics was washed with saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated to obtain the desired product in quantitative yields.

Workup

  1. distillationwas distilled off
  2. additionadded water
  3. extractionextracted with EtOAc (3×70 mL)
  4. washThe combined organics was washed with saturated NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-afcc2474341743ceb7f9a3ef4c9d2760
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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