Chlorotrimethylsilane → HCID 70984516, compound

HRID 339040Notes

Reaction equation

HRID 339040 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[Si](C)(C)[CH3:17]>CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([O:14][CH3:17])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 111947772-methylquinoline-8-carboxylic Acid

Product 1

HCID 70984516HCID 70984516, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methylquinoline-8-carboxylic acid (0.830 g, 4.43 mmol) in MeOH (20 mL) was added dropwise chlorotrimethylsilane (2.41 g, 22.2 mmol). The reaction mixture was heated at reflux overnight. After cooling, the reaction was concentrated under reduced pressure. The residue was dissolved in water and basified by dropwise addition of saturated aqueous NaHCO3 solution. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/EtOAc) to give methyl 2-methylquinoline-8-carboxylate (0.290 g, 33%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe reaction was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. additionbasified by dropwise addition of saturated aqueous NaHCO3 solution
  7. extractionThe mixture was extracted with EtOAc
  8. washThe combined organic layers were washed with brine
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography on silica gel (3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-6bf24ace13424249a93bc5e297f67827
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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