Trifluoroacetic acid → 4-(4-fluoroquinolin-2-yl)-N-methylaniline

HRID 452317Notes

Reaction equation

HRID 452317 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N:18](C)[C:19](=O)OC(C)(C)C)=[CH:14][CH:13]=2)[CH:3]=1.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH3:19])=[CH:14][CH:13]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58362549tert-Butyl methyl(4-(4-fluoroquinolin-2-yl)phenyl)carbamate

Product 1

HCID 583624894-(4-fluoroquinolin-2-yl)-N-methylanilineYield 55%

Procedure

tert-Butyl (4-(4-fluoroquinolin-2-yl)phenyl)(methyl)carbamate (4.5 mg, 0.013 mmol) was treated with TFA by using general procedure P. The crude product was purified by HPLC to afford T466 as an orange-colored solid (1.8 mg, 55%). 1H NMR (400 MHz, CDCl3): δ 8.57 (d, J=8.4 Hz, 1H), 8.02-7.97 (m, 3H), 7.75 (t, J=7.6 Hz, 1H), 7.56 (d, J=10.0 Hz, 1H), 6.72 (d, J=8.4 Hz, 2H), 2.95 (s, 3H); MS (ESI): 253 (M+H+).

Workup

  1. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-3be301e4fc7a43b0807c88023fcefbb6
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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