4-Chloroaniline → HCID 67290739, compound

HRID 1036872Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O)([O-:11])=[O:10].[CH3:20][C:21]([CH3:23])=[CH2:22]>C(#N)C.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][CH:14]([C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=1[N+:9]([O-:11])=[O:10])[CH2:20][C:21]2([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred suspension of 4-chloro-phenylamine (10.2 g, 80 mmol), 2-nitrobenzaldehyde (12.1 g, 80 mmol), and 2-methylpropene (25 ml, pre-cooled to −78° C.) in acetonitrile was added ytterbium trifluoromethanesulfonate (1.3 g, 2.1 mmol) at ice-bath. The resulting mixture was stirred at 80° C. for 16 h in sealed tube. The reaction mixture was cooled to 0° C. The mixture was concentrated in vacuum. The residue was diluted with water, extracted with diethyl ether. The extracts were washed with brine and then dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by column chromatography to give 6-chloro-4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (7.8 g, 30.8%). LC/MS m/e obsd. (ESI+) [(M+H)+] 317.1.

Workup

temperatureThe reaction mixture was cooled to 0° C
concentrationThe mixture was concentrated in vacuum
additionThe residue was diluted with water
extractionextracted with diethyl ether
washThe extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-b0f0ec95cbbc4c77a8f75fa9183977e7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546427B2

Reaction notes

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