Dichloromethane → HCID 66917198, compound

HRID 238343Notes

Reaction equation

HRID 238343 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:16]1[CH:20]=[CH:19][S:18][C:17]=1[CH:21]=[O:22])=[CH:6][NH:7]2.[BH4-].[Na+].ClCCl>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:16]1[CH:20]=[CH:19][S:18][C:17]=1[CH2:21][OH:22])=[CH:6][NH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 86641937HCID 86641937, compound

Product 1

HCID 66917198HCID 66917198, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(5-Fluoro-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl) thiophene-2-carbaldehyde (120 mg, 0.39 mmol) was suspended in ethanol (5 ml), and sodium borohydride (19.24 mg) was added to the suspension. The resulting mixture was stirred at room temperature for 1 hour. Dichloromethane was added to the reaction mixture, which was washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (dichloromethane:methanol=30:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to thereby obtain 110 mg of powdery white 5-fluoro-3-(2-hydroxymethylthiophen-3-yl)-8-propoxy-1H-quinolin-4-one (yield: 82%).

Workup

  1. washwas washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8debb58907904738ba0163c3086fe475
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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