4-Iodo-o-toluidine → 3-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid

Reaction equation

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

Participants

Reactant 2

HCID 832214-Iodo-o-toluidine

HCID 3453602-Fluoroisonicotinic acid

Product 1

HCID 576496173-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid

Procedure

synthesized as intermediate 1 by reacting 4.7 mmol of 2-methyl-4-iodoaniline with 7.0 mmol 2-fluoroisonicotinic acid. LC/MS [(5.3 min; 355 (M+1)]. See detailed procedure in Example 3.

Workup

customsynthesized as intermediate 1
custom5.3 min

Sources & evidence

ORD record: ord-6293048581e545d2bbc6a70e93acc1cf
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841459B2

Reaction notes

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