4-Chlorobenzaldehyde → HCID 118549298, compound

HRID 1501318Notes

Reaction equation

HRID 1501318 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl[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[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[CH3:33][C:29]1[C:30]([CH3:32])=[CH:31][C:26]2[N:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]3[O:17][CH:16]([C:15]3[CH:18]=[CH:19][CH:12]=[CH:13][CH:14]=3)[C:27]=2[CH:28]=1

Participants

7

Reactant 5

HCID 77264-ChlorobenzaldehydeHCID 8405IsoquinolineHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 11174787HCID 11174787, compound

Product 1

HCID 118549298HCID 118549298, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, treatment of isoquinoline (0.064 g, 59 μL, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 0.75 mmol) with 4,5-dimethyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.196 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=90/10) of the crude reaction mixture afforded 8,9-dimethyl-6-phenyl-4bH,6H-benzo[4,5][1,3]oxazino[2,3-a]isoquinoline as inseparable mixture of diastereomers as a yellow solid (0.127 g, 68% yield, dr determined by 1H NMR analysis of crude reaction mixture is 3:2).

Workup

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

Sources & evidence

ORD record
ord-0c867de9ee4f4963bdcd00f43ca40260
Source dataset
uspto-grants-2015_12
Patent number
US09206196B1

Reaction notes

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