Aniline → Methyl 2-anilinobenzoate

HRID 918807Notes

Reaction equation

HRID 918807 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=O)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:12][O:11][C:9](=[O:10])[C:8]1[C:7](=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 11011497methyl 2-trifluoromethanesulfonyloxybenzoate

Product 1

HCID 607074Methyl 2-anilinobenzoate

Procedure

Reaction of methyl 2-(trifluoromethanesulfonyloxy)benzoate with aniline according to general procedure A provided methyl ester of 2 as a yellow oil (99% yield). 1H NMR (CDCl3, 500 MHz): δ=9.48 (s, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.22-7.40 (m, 6H), 7.10 (t, J=7.3 Hz, 1H), 6.74 (t, J=7.5 Hz, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=169.1, 148.2, 141.0, 134.3, 131.8, 129.6, 123.8, 122.8, 117.3, 114.3, 112.2, 51.9.

Sources & evidence

ORD record
ord-f1b2e631d83945d9856db428c0d4a189
Source dataset
uspto-grants-2016_03
Patent number
US09271961B2

Reaction notes

Loading…