4-Aminobenzonitrile → HCID 58636706, compound

HRID 1158978Notes

Reaction equation

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

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636843HCID 58636843, compound

Product 1

HCID 58636706HCID 58636706, compoundYield 22.58%

Procedure

The reductive amination of 3-((5-formyl-2-methylpyridin-3-yloxy)methyl)benzonitrile (134) (300 mg, 1.2 mmol) and 4-aminobenzonitrile (422 mg, 3.6 mmol), as described in Example 21, gave 4-((5-(3-cyanobenzyloxy)-6-methylpyridin-3-yl)methylamino)benzonitrile (135) (95.24 mg, 22.58% yield).

Sources & evidence

ORD record: ord-0040b3b7bb504d4ba7900508b4c5affa
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

Loading…