Lithium iodide → HCID 71556820, compound

HRID 1497158Notes

Reaction equation

HRID 1497158 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH:25]([CH3:27])[CH3:26])=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1)=[CH:12][C:11]([Cl:23])=[CH:10][C:9]=2[Cl:24])=[O:4].[I-].[Li+]>N1C=CC=CC=1>[Cl:23][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([Cl:24])[CH:10]=1)[N:7]=[C:6]([CH:25]([CH3:26])[CH3:27])[C:5]([C:3]([OH:4])=[O:2])=[C:14]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 86682997HCID 86682997, compound

Product 1

HCID 71556820HCID 71556820, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6,8-dichloro-4-(3-chloro-4-fluoro-phenyl)-2-isopropyl-quinoline-3-carboxylic acid methyl ester (42.0 mg, 0.0984 mmol, Eq: 1.00) and lithium iodide (132 mg, 0.984 mmol, Eq: 10.0) in pyridine (1.5 ml) was heated to 135° C. overnight. The pyridine was then removed in vacuo and the remaining residue was diluted with water. The pH was adjusted to 12 by addition of 0.1N NaOH and the mixture was extracted with diethylether/heptane (60:40) (3×). The aqueous layer was acidified with 0.1N HCl to pH 3 and extracted with CHCl3 (3×). The combined CHCl3 layers were dried with Na2SO4 and evaporated to yield the title compound as white foam (35 mg). MS (ESI): 412.1 (M+H)+.

Workup

  1. customThe pyridine was then removed in vacuo
  2. additionthe remaining residue was diluted with water
  3. additionThe pH was adjusted to 12 by addition of 0.1N NaOH
  4. extractionthe mixture was extracted with diethylether/heptane (60:40) (3×)
  5. extractionextracted with CHCl3 (3×)
  6. dry with materialThe combined CHCl3 layers were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-fdac0a6243bf45dba4eb52a660c5cdad
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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