4-Aminobenzonitrile → HCID 58636761, compound

HRID 1158967Notes

Reaction equation

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

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 68644503HCID 68644503, compound

Product 1

HCID 58636761HCID 58636761, compoundYield 77%

Procedure

The reductive amination of 3-(5-carboxy-2,4-dimethyl-pyridin-3-yloxy)-benzonitrile (188 mg, 0.74 mmol) and 4-aminobenzonitrile (500 mg, 4.2 mmol), as described in Example 21, gave 4-{[3-(3-cyano-phenoxy)-2,4-dimethyl-pyridin-5-ylmethyl]-amino}-benzonitrile (95) (200 mg, 77% yield) as a brown oil.

Sources & evidence

ORD record: ord-f63a7fccf153471fb52ea14ee6b422ab
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

Loading…