4-Chlorobenzylamine → 3-[(4-Chlorobenzyl)amino]pyridine-4-carboxylic acid

HRID 1847149Notes

Reaction equation

HRID 1847149 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.F[C:11]1[CH:19]=[N:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:16]2[CH:17]=[N:18][CH:19]=[CH:11][C:12]=2[C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 817499513-[(4-Chlorobenzyl)amino]pyridine-4-carboxylic acidYield 32%

Procedure

The title compound was prepared in 32% yield from 4-chlorobenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.45 (br s, 1H), 8.04 (s, 1H), 7.76 (d, 1H, J=5.0 Hz), 7.51 (d, 1H, J=5.0 Hz), 7.29-7.36 (m, 4H), 4.51 (s, 2H). [M+H] calc'd for C13H11ClN2O2, 263, 265. Found 263, 265.

Sources & evidence

ORD record
ord-39dcf1b84c22440ca65c1898d959b25d
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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