Water → HCID 46203237, compound

HRID 1724865Notes

Reaction equation

HRID 1724865 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:14]=[C:13](Cl)[C:12]2[C:7](=[CH:8][C:9]([C:16]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][CH:11]=2)[N:6]=1.O>C1COCC1>[Cl:4][C:5]1[CH:14]=[C:13]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][C:9]([C:16]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 46203235HCID 46203235, compound

Product 1

HCID 46203237HCID 46203237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add sodium methoxide (4M, 1.1 mmol) to a solution of 2,4-dichloro-7-(3-trifluoromethyl-pyridin-2-yl)-quinoline (1.0 mmol) in THF (10 mL). Stir at room temperature for 1 hour, add water (15 mL) and extract with ethyl acetate. Wash the combined organic extracts with brine, dry (MgSO4) and evaporate. Purify the mixture of 2-chloro-4-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]quinoline and 4-chloro-2-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]quinoline by flash chromatography (elute with 1:2 hexane:ether) to give the title compound.

Workup

  1. extractionextract with ethyl acetate
  2. washWash the combined organic extracts with brine
  3. dry with materialdry (MgSO4)
  4. customevaporate
  5. customPurify
  6. additionthe mixture of 2-chloro-4-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]quinoline and 4-chloro-2-methoxy-7-[3-(trifluoromethyl)pyridin-2-yl]quinoline
  7. washby flash chromatography (elute with 1:2 hexane:ether)

Sources & evidence

ORD record
ord-f4c0934eccc541d9ace2d3870392167c
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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