(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-amine → 4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine

HRID 1696745Notes

Reaction equation

COC1C=CC(C[NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:10]=2)=CC=1>OS(O)(=O)=O>[F:18][C:15]([F:16])([F:17])[C:13]1[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=2)[N:10]=[C:9]([NH2:8])[CH:14]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To (4-methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-amine (6.4 g, 15 mmol) immersed in an icebath was added icecold conc. H2SO4 (30 mL) [immediate development of a deep red color!] and the mixture was stirred at 5° C. for 5 min, then the cooling bath was removed and stirring was continued at 23° C. for 2 h until all gummy material had dissolved into a clear deep red solution. Poured onto ice, made alkaline with 32% NaOH-sol., saturated with solid NaCI, extracted thrice with THF/TBME, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a light yellow solid (4.537 g, 99%). MS (ISP) 307.1 [(M+H)+].

Workup

customthe cooling bath was removed
stirringstirring
waitwas continued at 23° C. for 2 h until all gummy material
dissolutionhad dissolved into a clear deep red solution
additionPoured onto ice
extraction, saturated with solid NaCI, extracted thrice with THF/TBME
dry with materialdried over Na2SO4
customRemoval of the solvent in vacuum
waitleft the title compound as a light yellow solid (4.537 g, 99%)

Sources & evidence

ORD record: ord-a93e7ba8dc7d43069d88d0bfd055488e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163778B2

Reaction notes

Loading…