Aniline → Methyl 3-(phenylamino)benzoate

HRID 918808

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][CH:16]=[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][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

Reactant 2

HCID 6115Aniline

HCID 12070Methyl 3-bromobenzoate

Product 1

HCID 614856Methyl 3-(phenylamino)benzoate

Procedure

Reaction of methyl 3-bromobenzoate with aniline according to general procedure A provided methyl ester of Compound 3 as a yellow oil (94% yield). 1H NMR (CDCl3, 500 MHz): δ=7.73 (s, 1H), 7.56 (d, J=7.6 Hz, 1H), 7.22-7.35 (m, 4H), 7.10 (d, J=8.5 Hz, 2H), 7.00 (t, J=7.4 Hz, 1H), 5.81 (s, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.3, 143.9, 142.6, 131.6, 129.7, 129.6, 122.0, 121.9, 121.7, 118.7, 118.4, 52.3.

Sources & evidence

ORD record: ord-605c2488ebc24d648db00545c3d7ce2a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271961B2

Linked notes

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