Water → HCID 178515542, compound

HRID 1677123Notes

Reaction equation

HRID 1677123 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.[Cl-].[Al+3].[Cl-].[Cl-].[BH4-].[Na+].O>O1CCCC1>[CH2:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]([F:15])([F:13])[F:14])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 178519486HCID 178519486, compound

Product 1

HCID 178515542HCID 178515542, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-hydroxy-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (17.0 g, 53.7 mmol) in tetrahydrofuran (270 mL), aluminum chloride (35.1 g, 263 mmol) and sodium borohydride (5.49 g, 145 mmol) were added at 0° C., stirred at room temperature for 30 minutes, and then refluxed for 5 hours. The reaction solution was brought to 0° C., added with water, and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was recrystallized with ethyl acetate, and the title compound (11.7 g, yield 72%) was obtained as a colorless crystal.

Workup

  1. temperaturerefluxed for 5 hours
  2. customwas brought to 0° C.
  3. extractionextracted with ethyl acetate
  4. washSubsequently, the organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-4ce3a01b41ea4d628d04b0407023bc05
Source dataset
uspto-grants-2011_08
Patent number
US08008306B2

Reaction notes

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