5,6,7,8-Tetrahydroquinoline → 5,6,7,8-Tetrahydro-1-quinoliniumolate

HRID 499390Notes

Reaction equation

HRID 499390 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(OCC)(=O)C>[N+:1]1([O-:19])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 663355,6,7,8-TetrahydroquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolateYield 101.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5,6,7,8-Tetrahydroquinoline (3.0 g, 22.5 mmol) was dissolved in ethyl acetate (15 ml), and 3-chloroperbenzoic acid (ca. 70%, 5.6 g, 22.5 mmol) was added thereto. The reaction mixture was stirred at room temperature for 2 days, subjected to a silica gel column chromatography and eluted with ethyl acetate-ethanol (5:1, v/v) to give the titled compound (3.4 g, 97%).

Workup

  1. washeluted with ethyl acetate-ethanol (5:1

Sources & evidence

ORD record
ord-a2dc6b7538394112adecf198a26ade73
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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