Aniline → Methyl 4-anilinobenzoate

HRID 918809Notes

Reaction equation

HRID 918809 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 12081Methyl 4-bromobenzoate

Product 1

HCID 614877Methyl 4-anilinobenzoate

Procedure

Reaction of methyl 4-bromobenzoate with aniline according to general procedure A provided methyl ester of Compound 4 as a yellow oil (84% yield). 1H NMR (CDCl3, 500 MHz): δ=7.92 (d, J=8.8 Hz, 2H), 7.32-7.38 (m, 2H), 7.18 (d, J=7.5 Hz, 2H), 7.09 (m, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.02 (s, 1H), 3.89 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.2, 148.3, 141.1, 131.7, 129.7, 123.4, 121.5, 120.7, 114.9, 51.9.

Sources & evidence

ORD record
ord-5980c2c4ec534a13a0589e24030e878c
Source dataset
uspto-grants-2016_03
Patent number
US09271961B2

Reaction notes

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