Phosphorus oxychloride → HCID 86718154, compound

HRID 2205171Notes

Reaction equation

HRID 2205171 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:3]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.O=P(Cl)(Cl)[Cl:35]>>[Cl:35][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:3]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468668HCID 178468668, compound

Product 1

HCID 86718154HCID 86718154, compoundYield 77%

Procedure

A solution of ethyl 4-hydroxy-2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate (1 g, 2.33 mmol, 1.00 equiv) in POCl3 (10 mL) was heated to reflux for 4 h in an oil bath. The resulting mixture was concentrated under vacuum, then diluted with 30 mL of ethyl acetate, and washed with 1×50 mL of sodium bicarbonate (aq.). The organic layer was concentrated under vacuum and purified by column chromatography (ethyl acetate/petroleum ether (1:10)) yielding 0.8 g (77%) of ethyl 4-chloro-2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate as a yellow solid.

Workup

  1. temperatureto reflux for 4 h in an oil bath
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additiondiluted with 30 mL of ethyl acetate
  4. washwashed with 1×50 mL of sodium bicarbonate (aq.)
  5. concentrationThe organic layer was concentrated under vacuum
  6. custompurified by column chromatography (ethyl acetate/petroleum ether (1:10))

Sources & evidence

ORD record
ord-7695126949234f2ca68ea828f33ea2f2
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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