Boron trifluoride etherate → HCID 67292481, compound

HRID 1036906Notes

Reaction equation

[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]=[N:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1)([O-:3])=[O:2].[CH3:23][C:24]([CH3:26])=[CH2:25].B(F)(F)F.CCOCC>C(#N)C>[CH3:23][C:24]1([CH3:26])[C:18]2[C:8](=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:17]=2)[NH:7][CH:6]([C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:25]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 4-(2-nitrobenzylideneamino)benzoate (18.67 g, 62.6 mmol) in acetonitrile was added 2-methylpropene (80 mL, pre-cooled to −78° C.) and boron trifluoride etherate (1 mL) at ice-bath. The reaction mixture was stirred at 90° C. for 18 h in sealed tube. The reaction mixture was concentrated in vacuo. The residue was purified by flash column chromatography to give ethyl 4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as yellow solid (13.4 g, yield 60.4%). %). LC/MS m/e obsd. (ESI+) [(M+H)+] 355.1.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-5752dcca6f7c4285ab2eeb54cfabcb73
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546427B2

Reaction notes

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