2-(Aminomethyl)aniline → 3-[(2-Aminobenzyl)amino]pyridine-4-carboxylic acid

HRID 63055

Reaction equation

HRID 63055 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].F[C:11]1[CH:19]=[N:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:16]1[CH:17]=[N:18][CH:19]=[CH:11][C:12]=1[C:13]([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 1780962-(Aminomethyl)anilineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 771059103-[(2-Aminobenzyl)amino]pyridine-4-carboxylic acidYield 9%

Procedure

The title compound was prepared in 9% yield from 2-aminobenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.16 (s, 1H), 7.82 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.05 (d, 1H, J=7.5 Hz), 6.97 (td, 1H, J=7.8, 1.4 Hz), 6.66 (d, 1H, J=7.9 Hz), 6.52 (td, 1H, J=7.4, 1.0 Hz), 4.35 (s, 2H). [M+H] calc'd for C13H13N3O2, 244. found 244.

Sources & evidence

ORD record
ord-a6c8efd0809845a2a9fc11e3939ca554
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Linked notes

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