4-Aminobenzonitrile → HCID 58636812, compound

HRID 1158968Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][O:7][C:8]1[C:9]([CH3:18])=[N:10][CH:11]=[C:12]([CH:16]=O)[C:13]=1[CH2:14][CH3:15])#[N:2].[NH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([NH:22][CH2:16][C:12]2[C:13]([CH2:14][CH3:15])=[C:8]([O:7][CH2:6][C:5]3[CH:4]=[C:3]([CH:21]=[CH:20][CH:19]=3)[C:1]#[N:2])[C:9]([CH3:18])=[N:10][CH:11]=2)=[CH:24][CH:25]=1)#[N:28]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636752HCID 58636752, compound

Product 1

HCID 58636812HCID 58636812, compoundYield 52.3%

Procedure

The reductive amination of 3-(3-cyano-benzyloxy)-4-ethyl-2-methyl-pyridine-5-carbaldehyde (101) (700 mg, 2.50 mmol) and 4-aminobenzonitrile (2.0 g, 16.9 mmol), as described in Example 21, gave 3-{5-[(4-cyano-phenylamino)-methyl]-4-ethyl-2-methyl-pyridin-3-yloxymethyl}-benzonitrile (102) (500 mg, 52% yield).

Sources & evidence

ORD record: ord-4d105ecab23343debf2411a3a1d08bad
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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