2-Methylpyridine → HCID 10695549, compound

HRID 1387808Notes

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.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]>CN(C=O)C>[Cl-:1].[CH3:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N+:28]=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

Participants

Conditions

Temperature: 70 °C

Procedure

In DMF (3 ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (160 mg), and to the mixture was added 2-picoline (126 μl). The mixture was stirred at 70° C. for 63 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 2-methyl-1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]pyridinium chloride (Compound 28) (140 mg) as pale brown crystals.

Workup

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

Sources & evidence

ORD record: ord-d4393ac8a50a4b0a8613b364a70ebad5
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268354B1

Reaction notes

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