Aniline → 1,2-Dihydroquinoline

HRID 568178Notes

Reaction equation

HRID 568178 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[CH2:13]CCC[CH2:9]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.B(F)(F)F.CCOCC.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[La+3]>CCC(=O)CC.CC(C)=O>[NH:1]1[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=[CH:8][CH2:13]1

Participants

8

Reactant 5

HCID 6115AnilineHCID 7967CyclohexanoneHCID 8000Boron trifluoride etherateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2733938Lanthanum tris(trifluoromethanesulfonate)

Product 1

HCID 52314021,2-Dihydroquinoline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7288Ethyl ketoneSolvent

Procedure

In the final step of this novel process, an aniline 10 is treated with a ketone 11, especially acetone, cyclohexanone or 3-pentanone, in the presence of a catalyst, especially camphor sulfonic acid, boron trifluoride etherate or lanthanum tris(trifluoromethanesulfonate), to afford the 1,2-dihydroquinoline 12:

Sources & evidence

ORD record
ord-a9179c3b7ed743a393450609545a9d53
Source dataset
uspto-grants-2001_01
Patent number
US06180794B2

Reaction notes

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