Hydrochloric Acid → HCID 18790540, compound

HRID 1106984Notes

Reaction equation

HRID 1106984 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[O:24])[CH2:12][S:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1.[BH4-].[Na+].O.Cl>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:24])[CH2:12][S:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 18790579HCID 18790579, compound2×

Product 1

HCID 18790540HCID 18790540, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-15 °C

Procedure

4-[2-(2-Naphtyl)-2-oxoethylthio]quinoline (Compound 2; 450 mg, 1.37 mmol) was dissolved in ethanol (50 ml), added at -15° C. with sodium borohydride (70 mg, 3.04 mmol), and stirred at -15° C. for two hours. The reaction mixture was added with water and neutralized by 2N hydrochloric acid. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed by silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 165.7 mg of the titled compound (36.5%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washwashed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-85a42bac711e4b0d89192a55405d0747
Source dataset
uspto-grants-2000_05
Patent number
US06057447

Reaction notes

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