4-Aminobenzonitrile → HCID 68644193, compound

HRID 1158941Notes

Reaction equation

[CH:1]([C:3]1[C:4]([CH3:20])=[C:5]([O:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[C:6]([CH3:9])=[N:7][CH:8]=1)=O.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][O:10][C:5]2[C:4]([CH3:20])=[C:3]([CH2:1][NH:21][C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)[CH:8]=[N:7][C:6]=2[CH3:9])=[CH:13][CH:14]=1)#[N:17]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 86240729HCID 86240729, compound

Product 1

HCID 68644193HCID 68644193, compoundYield 82.1%

Procedure

The reductive amination of 4-(5-formyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile (23) (2.3 g, 8.6 mmol) and 4-aminobenzonitrile (4.4 g, 37.2 mmol), as described in Example 21, gave 4-{[5-(4-cyano-benzyloxy)-4,6-dimethyl-pyridin-3-ylmethyl]-amino}-benzonitrile (30) (2.6 g, 82% yield) as a colorless solid.

Sources & evidence

ORD record: ord-1e845dae5c4346dba47e7f940ba9d58e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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