Trifluoroacetic acid → N-Methyl-4-(quinolin-3-yl)aniline

HRID 452319Notes

Reaction equation

HRID 452319 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][CH:11]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:1][NH:2][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66700372Tert-butyl methyl(4-(quinolin-3-yl)phenyl)carbamate

Product 1

HCID 58362565N-Methyl-4-(quinolin-3-yl)aniline

Procedure

tert-Butyl methyl(4-(quinolin-3-yl)phenyl)carbamate (44 mg, 0.13 mmol) was then treated with TFA by using the general procedure P. The crude product was purified by HPLC to afford T477 as an orange-colored wax (13 mg, 29%). 1H NMR (400 MHz, CDCl3): δ 9.46 (d, J=2.0 Hz, 1H), 8.79 (d, J=1.6 Hz, 1H), 8.47 (d, J=8.4 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 7.95 (m, 1H), 7.83 (m, 1H), 7.62 (m, 2H), 6.82 (m, 2H), 2.94 (s, 3H); MS (ESI): 235 (M+H+).

Workup

  1. customThe crude product was purified by HPLC
  2. customto afford T477 as an orange-colored wax (13 mg, 29%)

Sources & evidence

ORD record
ord-0a5d5fd79a764cab95d1fdee1aa742f6
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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