Chromic Acid → 3-(5-Fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

HRID 1867232Notes

Reaction equation

HRID 1867232 reaction equation
[Cr](O)(O)(=O)=O.[F:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][C:10]([CH3:28])([CH3:27])[N:11]=[C:12]2[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.S([O-])([O-])=[O:30].[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C(O)(=O)C>[F:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=[O:30])[C:10]([CH3:28])([CH3:27])[N:11]=[C:12]2[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

7

Reactant 4

HCID 24425Chromic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 11231977HCID 11231977, compound

Product 1

HCID 231608453-(5-Fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolineYield 6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Chromic acid (4.9 g) was added to an acetic acid (50 mL) solution of 3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (5.0 g, 16.4 mmol), followed by heating and refluxing for 14 hours, pouring water, aqueous sodium sulfite solution and aqueous sodium hydrogencarbonate solution. After stirring for 30 minutes, extracting with ethyl acetate, and applying the resulting residue to chromatography to obtain 0.3 g (yield 6%) of the target compound.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 14 hours
  3. extractionextracting with ethyl acetate

Sources & evidence

ORD record
ord-e9d8a644b16245e680f45e2857678cd8
Source dataset
uspto-grants-2009_12
Patent number
US07632783B2

Reaction notes

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