Phosphorus oxychloride → Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

HRID 2410148Notes

Reaction equation

HRID 2410148 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469588HCID 178469588, compound

Product 1

HCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylateYield 97%

Procedure

A solution of ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate (Example Ac, 1.24 g, 5.0 mmol) in POCl3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale-yellow solid (1.29 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ 1.36 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 7.57 (d, J=2.8 Hz, 1H), 7.61 (dd, J=2.8, 8.8 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).

Workup

  1. customwas refluxed under nitrogen for 3 hrs
  2. customevaporated under reduced pressure
  3. customThe residue was carefully quenched with ice
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with cold water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a3eb67465443428f85f9acf28aecd98a
Source dataset
uspto-grants-2014_08
Patent number
US08815956B2

Reaction notes

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