4-Cyanopyridine → HCID 18472409, compound

HRID 565870Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[C:28]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)#[N:29]>CN(C=O)C>[Cl-:1].[C:28]([C:30]1[CH:35]=[CH:34][N+:33]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]3[CH2:21][CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:17][CH:18]=4)[CH:13]=3)=[O:11])=[CH:5][CH:4]=2)=[CH:32][CH:31]=1)#[N:29]

Participants

Conditions

Temperature: 70 °C

Procedure

In DMF (3ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (140mg), and to the mixture was added 4-cyanopyridine (117mg). The mixture was stirred at 70° C. for 24 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 4-cyano-1-[4-(7-phenyl-3,4-dihydro-naphthalene-2-carboxamido)benzyl]pyridinium chloride (Compound 21) (141mg) as pale brown crystals.

Workup

concentrationconcentrated under reduced pressure
customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record: ord-03a335aa77514c96a5aaa57f614fc494
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172061B2

Reaction notes

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