2,5-Dimethylaniline → HCID 10517305, compound

HRID 1952889Notes

Reaction equation

HRID 1952889 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][C:15]1[C:16]([CH3:22])=[CH:17][CH:18]=[C:19]([CH3:21])[CH:20]=1>>[CH3:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[NH:14][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 72592,5-DimethylanilineHCID 684522-Bromo-3-nitrobenzoic acid

Product 1

HCID 10517305HCID 10517305, compoundYield 65%

Procedure

Reaction of 2-bromo-3-nitrobenzoic acid and 2,5-xylidine gave 2-(2,5-dimethyl phenylamino)-3-nitro benzoic acid (65%): mp (benzene/acetone) 215-217° C. 1H NMR [(CD3)2SO] δ 2.10 (s, 3 H, CH3), 2.23 (s, 3 H, CH3), 6.53 (s, 1H, H-6'), 6.79 (d, J=7.4 Hz, 1 H, H-4'), 7.02 (t, J=8.0 Hz, 1 H, H-5), 7.11 (d, J=7.7 Hz, 1 H, H-3'), 8.03 (dd, J=8.1, 1.4 Hz, 1 H, H-6), 8.22 (dd, J=7.7, 1.5 Hz, 1 H, H-4), 9.84 (br s, 1 H, NH), 13.8 (br s, 1 H, CO2H). Anal. (C15H14N2O4) C, H, N.

Sources & evidence

ORD record
ord-5488bfad8fc64ca198f6d60e86ca9911
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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