2-Hydroxyquinoline → HCID 19387693, compound

HRID 1757375Notes

Reaction equation

HRID 1757375 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C2[C:18](=CC=CC=2)[CH:17]=[CH:16][C:15]1=[O:24].[Cl-].ClC1C=CC2C(=CC=CC=2)[N+]=1C1CCCCC1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C[N+]1C2C=CC=CC=2SC=1SC.C(N(CC)CC)C>>[CH:8]1([N:7]2[C:1]3[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]([CH3:18])=[CH:16][C:15]2=[O:24])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 5

HCID 60382-HydroxyquinolineHCID 8471TriethylamineHCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)HCID 74567N-CyclohexylanilineHCID 19387694HCID 19387694, compound

Product 1

HCID 19387693HCID 19387693, compound

Procedure

1-Cyclohexyl-1,2-dihydro-4-methyl-2-quinolone is prepared using N-cyclohexylaniline as starting material. The quinolone (0.482 g, 2 mmol) is transformed to the 2-chloro-1-cyclohexylquinolinium chloride with a procedure similar to Example 3, and is then reacted with 3-methyl-2-methylthiobenzothiazolium tosylate (0.74 g, 2 mmol) and triethylamine (0.28 mL, 2 mmol) to yield the product.

Workup

  1. customto yield the product

Sources & evidence

ORD record
ord-b267233e487c48408ca248b9f00031fd
Source dataset
uspto-grants-1995_08
Patent number
US05445946

Reaction notes

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