p-Toluidine → Methyl 3-(4-methylanilino)benzoate

HRID 918817Notes

Reaction equation

HRID 918817 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 12070Methyl 3-bromobenzoate

Product 1

HCID 70911895Methyl 3-(4-methylanilino)benzoate

Procedure

Reaction of methyl 3-bromobenzoate with p-toluidine according to general procedure A provided methyl ester of Compound 12 as a yellow oil (69% yield). 1H NMR (CDCl3, 500 MHz): δ=7.68 (s, 1H), 7.55 (d, J=7.6 Hz, 1H), 7.29 (t, J=7.7 Hz, 1H), 7.19 (m, 1H), 7.13 (d, J=8.0 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 5.77 (s, 1H), 3.91 (s, 3H), 2.34 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.4, 144.6, 139.8, 131.9, 131.5, 130.2, 129.5, 121.3, 120.8, 119.7, 117.5, 52.2, 20.9.

Sources & evidence

ORD record
ord-7cfddc7b75914ac99b24f11e252adaf8
Source dataset
uspto-grants-2016_03
Patent number
US09271961B2

Reaction notes

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