Ethyl chloroformate → 8-Methyl-2-(propylsulfanyl)quinoline-3-carbaldehyde

HRID 1911791Notes

Reaction equation

HRID 1911791 reaction equation
ClC([O:4][CH2:5][CH3:6])=O.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CNCC1[C:22]([S:32][CH2:33][CH2:34][CH3:35])=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:31]>C1COCC1.C(Cl)Cl>[CH3:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:24]=1[N:23]=[C:22]([S:32][CH2:33][CH2:34][CH3:35])[C:6]([CH:5]=[O:4])=[CH:31]2

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 57486861HCID 57486861, compound

Product 1

HCID 574444608-Methyl-2-(propylsulfanyl)quinoline-3-carbaldehydeYield 229%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl chloroformate (0.4 ml, 4.2 mmol) and potassium carbonate (0.875 g, 6.3 mmol) were added to (3,5-bis-trifluoromethyl-benzyl)-(8-methyl-2-propylsulfanyl-quinolin-3-ylmethyl)-amine (1.058 g, 2.1 mmol) which was dissolved in anhydrous THF (10 mL). The resulting mixture was stirred at room temperature for overnight. The mixture was diluted with methylene chloride, and was washed one time with water. The organic phase was dried over potassium carbonate and concentrated by rotary evaporation. The resulting sample was dried under vacuum gave a light yellow solid (1.18 g, 97%).

Workup

  1. washwas washed one time with water
  2. dry with materialThe organic phase was dried over potassium carbonate
  3. concentrationconcentrated by rotary evaporation
  4. customThe resulting sample was dried under vacuum

Sources & evidence

ORD record
ord-d83069ab495941e694f039686a04bcb3
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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