Sodium Bicarbonate → HCID 70873495, compound

HRID 2172228Notes

Reaction equation

HRID 2172228 reaction equation
C(O)C.Cl.O1CCCCC1[O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)[CH:16]=[CH:15]2.C(=O)([O-])O.[Na+]>C(O)C>[F:33][C:31]([F:32])([F:34])[O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:17]2[CH:16]=[CH:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([OH:11])[CH:13]=3)[N:18]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 70873649HCID 70873649, compound

Product 1

HCID 70873495HCID 70873495, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1 N hydrochloric acid ethanol solution (40 ml) was added to an ethanol (10 ml) solution of 6-(Tetrahydro-2H-pyran-2-yloxy)-2-[4-(trifluoromethoxy)benzyloxy]quinoline (3.5 g, 8.3 mmol) and then stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure, and the resulting crude crystal was washed with hexane-diethylether to afford the title compound as a white powder (2.52 g, yield 90%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtering
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washthe resulting crude crystal was washed with hexane-diethylether

Sources & evidence

ORD record
ord-21f66715ff4d4ce78429caf6dff3cf4b
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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