4-Chlorobenzylamine → Methyl 3-[(4-chlorobenzyl)amino]pyridine-4-carboxylate

HRID 63043Notes

Reaction equation

HRID 63043 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.Br[C:11]1[CH:20]=[N:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:17]2[CH:18]=[N:19][CH:20]=[CH:11][C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 2762700Methyl 3-bromoisonicotinate

Product 1

HCID 86728197Methyl 3-[(4-chlorobenzyl)amino]pyridine-4-carboxylateYield 72%

Procedure

The title compound was prepared in 72% yield from 4-chlorobenzylamine and methyl 3-bromoisonicotinate according to the procedure for Preparation 4A. 1H NMR (400 MHz, CDCl3): δ 8.14 (s, 1H), 7.94 (d, 1H, J=5.0 Hz), 7.82 (br s, 1H), 7.62 (d, 1H, J=5.0 Hz), 7.24-7.32 (m, 4H), 4.47 (d, 2H, J=5.7 Hz), 3.89 (s, 3H). [M+H] calc'd for C14H13ClN2O2, 277, 279. found 277, 279.

Sources & evidence

ORD record
ord-0fdb754a241c45b987bdb8e986160b00
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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