Phosphorus oxychloride → Methyl 2-chloroquinoline-6-carboxylate

HRID 2080145Notes

Reaction equation

HRID 2080145 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N+:16]([O-])=[CH:15][CH:14]=[CH:13]2)=[O:9]>C(OCC)(=O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([Cl:3])[CH:14]=[CH:13]2)=[O:9]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21707072Methyl quinoline-6-carboxylate 1-oxide

Product 1

HCID 56924381Methyl 2-chloroquinoline-6-carboxylateYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (10 mL) was added to quinoline-6-carboxylic acid methyl ester N-oxide (1.5 g, 7.6 mmol), and the solution was refluxed for 2 hours. The reaction solution was poured onto an ice, and warmed gradually to room temperature. Ethyl acetate was added to the reaction solution, which was then extracted, and sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (0.47 g, 2.1 mmol, 28%) was obtained as a white solid.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. extractionwas then extracted
  3. washsequentially washed with an aqueous solution of saturated sodium bicarbonate and brine
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5c7e6d15a87a4e569ee274eece6fa371
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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