Sodium Bicarbonate → HCID 67402088, compound

HRID 1186456Notes

Reaction equation

HRID 1186456 reaction equation
[N+:1]([C:4]1[C:5]([O:14][CH:15]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:16]([F:19])([F:18])[F:17])=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:19][C:16]([F:17])([F:18])[CH:15]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[O:14][C:5]1[C:4]([NH2:1])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67401697HCID 67401697, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 67402088HCID 67402088, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

3-Nitro-2-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]quinoline (253 mg, 0.720 mmol) obtained in Step 3 was dissolved in ethanol (12.7 mL). To this, tin chloride dihydrate (817 mg, 3.62 mmol) was added and the mixture was stirred at 90° C. for 1 hour. By addition of an aqueous sodium bicarbonate solution to neutralize the reaction mixture, the reaction was stopped. Then, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/1) to give Compound HF (182 mg, yield: 79%).

Workup

  1. extractionThen, extraction with ethyl acetate
  2. washby washing with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/1)
  6. customto give Compound HF (182 mg, yield: 79%)

Sources & evidence

ORD record
ord-ac22978cdcb94e8ca2111fcaf631622e
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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