Phosphorus oxychloride → Ethyl 4-chloro-7-fluoroquinoline-3-carboxylate

HRID 1466982Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178469609Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 14219731Ethyl 4-chloro-7-fluoroquinoline-3-carboxylate

Procedure

Prepared as in Example 1b from ethyl 7-fluoro-4-hydroxyquinoline-3-carboxylate (Example 9c) and POCl3 as an off white solid (96%). MS 254, 256 (MH+).

Sources & evidence

ORD record: ord-7ade9cf03f2f4b6397f751974e5dcea8
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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