P-Anisidine → Methyl 3-(4-methoxyanilino)benzoate

HRID 918816Notes

Reaction equation

HRID 918816 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].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 12070Methyl 3-bromobenzoate

Product 1

HCID 22492538Methyl 3-(4-methoxyanilino)benzoate

Procedure

Reaction of methyl 3-bromobenzoate with p-anisidine according to general procedure A provided methyl ester of Compound 11 as a yellow oil (93% yield). 1H NMR (CDCl3, 500 MHz): δ=7.57 (s, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.28 (m, 1H), 7.07-7.12 (m, 3H), 6.90 (d, J=8.8 Hz, 2H), 5.62 (s, 1H), 3.90 (s, 3H), 3.83 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=167.5, 156.0, 145.8, 135.2, 131.5, 129.5, 123.1, 120.7, 119.7, 116.4, 115.0, 55.8, 52.2.

Sources & evidence

ORD record
ord-1f9d7e46ddc94432a802c2f7ed4a4714
Source dataset
uspto-grants-2016_03
Patent number
US09271961B2

Reaction notes

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