Quinoline → HCID 118549281, compound

HRID 1501306Notes

Reaction equation

HRID 1501306 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.FC(F)(F)S(O[C:26]1[C:34]([Si](C)(C)C)=[CH:33][C:29]2[O:30][CH2:31][O:32][C:28]=2[CH:27]=1)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[O:17][CH:2]3[CH:3]=[CH:4][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=4[N:1]3[C:26]3[CH:27]=[C:28]4[O:32][CH2:31][O:30][C:29]4=[CH:33][C:34]2=3)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 7047QuinolineHCID 77264-ChlorobenzaldehydeHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 11210047HCID 11210047, compound

Product 1

HCID 118549281HCID 118549281, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 0.75 mmol) with 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl trifluoromethanesulfonate (0.205 g, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=70/30) of the crude reaction mixture afforded 8-(4-chlorophenyl)-6aH,8H [1,3]dioxolo[4″,5″:4′,5′]benzo[1′,2′:4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a white solid (0.171 g, 88% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

Workup

  1. customat −10° C. to room temperature
  2. customfor 12 hrs
  3. customreaction mixture

Sources & evidence

ORD record
ord-a382bcdf86ed46509718f677b08554db
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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