4-Chloroaniline → Methyl 3-[(4-chlorophenyl)amino]benzoate

HRID 918813Notes

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].[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[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:17][C:16]2[CH:18]=[CH:19][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH:3]=1

Participants

Reactant 2

HCID 78124-Chloroaniline

HCID 12070Methyl 3-bromobenzoate

Product 1

HCID 69610928Methyl 3-[(4-chlorophenyl)amino]benzoate

Procedure

Reaction of methyl 3-bromobenzoate with 4-chloroaniline according to general procedure A provided methyl ester of Compound 8 as a yellow oil (52% yield). 1H NMR (CDCl3, 500 MHz): δ=7.70 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.33 (t, J=7.9 Hz, 1H), 7.21-7.27 (m, 3H), 7.01 (d, J=8.8 Hz, 2H), 5.78 (s, 1H), 3.91 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.2, 143.4, 141.4, 131.7, 129.7, 126.7, 122.5, 122.0, 119.8, 118.7, 52.4.

Sources & evidence

ORD record: ord-a1dfc5440521411a8d5207f4a57f086e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271961B2

Reaction notes

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