p-Toluidine → HCID 67290538, compound

HRID 1036902Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.[CH2:18]=[C:19]([CH3:21])[CH3:20].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[CH2:18][C:19]([CH3:21])([CH3:20])[C:6]3[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:7]=3)[NH:8]2)[CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-methyl-phenylamine (6.8 g, 64.0 mmol) and 3-bromobenzaldehyde (7.5 mL, 64.0 mmol) in acetonitrile (150 mL) were added isobutene (18.7 mL, 256.7 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (4.7 g, 7.7 mmol). The resulting mixture was stirred at 85° C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinoline (8.5 g, 40.0%) as a light yellow solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 330.0 & 332.0.

Workup

washwashed with water (100 mL×2) and brine (100 mL×2)
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed in vacuo
customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-e7f84c902f2a428ebf642c93d562f5cf
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546427B2

Reaction notes

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