Phosphorus oxychloride → Methyl 4-chloro-8-fluoro-7-methylquinoline-2-carboxylate

HRID 922796Notes

Reaction equation

HRID 922796 reaction equation
[F:1][C:2]1[C:3]([CH3:17])=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][C:7]2=O.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:7]1[C:6]2[C:11](=[C:2]([F:1])[C:3]([CH3:17])=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89543481Methyl 8-fluoro-4-hydroxy-7-methylquinoline-2-carboxylate

Product 1

HCID 89543858Methyl 4-chloro-8-fluoro-7-methylquinoline-2-carboxylateYield 75%

Procedure

Methyl 8-fluoro-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (7-7, 1.23 g, 5.23 mmol) in POCl3 (11 ml) was heated at 100° C. for 1 hour. The excess POCl3 was removed in vacuo. The resulting residue was triturated with ether, then filtered and washed with ether till no brown color remained in the ether. The remaining solid was Methyl 4-chloro-8-fluoro-7-methylquinoline-2-carboxylate (7-8, 993 mg, 75% yield) 100% pure by LCMS, LRMS m/z (M+H)+ 254.0 found, 254.1 required.

Workup

  1. customThe excess POCl3 was removed in vacuo
  2. customThe resulting residue was triturated with ether
  3. filtrationfiltered
  4. washwashed with ether till no brown color

Sources & evidence

ORD record
ord-a3e17e7615dc436a8f8d26fcb4ba39a8
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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