Quinoline → HCID 118549297, compound

HRID 1501297Notes

Reaction equation

HRID 1501297 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:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH:15]=[O:16].FC(F)(F)S(O[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[Cl:11][C:12]1[CH:13]=[C:14]([CH:15]2[O:16][CH:2]3[CH:3]=[CH:4][C:5]4[C:10]([N:1]3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

7

Reactant 5

HCID 7047QuinolineHCID 227103,4-DichlorobenzaldehydeHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Product 1

HCID 118549297HCID 118549297, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and 3,4-dichlorobenzaldehyde (0.130 g, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 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=75/25) of the crude reaction mixture afforded 5-(3,4-dichlorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as a yellow solid (0.127 g, 67% 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-6a154110ffe74ee5991b3731edd0e440
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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