Ethyl 6-chloro-4-hydroxy-3-quinolinecarboxylate → Ethyl 4,6-dichloroquinoline-3-carboxylate

HRID 336865

Reaction equation

HRID 336865 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].O(Cl)[Cl:19].[P+5]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:19])=[CH:13][C:12]([Cl:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 718113Ethyl 6-chloro-4-hydroxy-3-quinolinecarboxylateHCID 178479711HCID 178479711, compound

Product 1

HCID 1479087Ethyl 4,6-dichloroquinoline-3-carboxylate

Conditions

Temperature
125 °C

Procedure

Ethyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate (19.8 mmol) and phosphorus (V) oxychloride (99.3 mmol) was stirred and heated to 125° C. for 12 hours. The mixture was cooled to ambient temperature and the phosphorus (V) oxychloride was evaporated. The crude product was used without further purification. MS m/z 271.80 (M+1).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe phosphorus (V) oxychloride was evaporated
  3. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-7f5f899c7f9c44a4b10cfe57c6ae087e
Source dataset
uspto-grants-2014_11
Patent number
US08889706B2

Linked notes

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