5-(Aminomethyl)-2-(trifluoromethyl)pyridine → 2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5-nitroisoquinolin-1(2H)-one

HRID 1037777Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[N+:13]([C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][O:20][C:21]2=O)([O-:15])=[O:14]>CO>[F:12][C:2]([F:11])([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[CH:25][C:16]=3[N+:13]([O-:15])=[O:14])[C:21]2=[O:20])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

C-(6-Trifluoromethyl-pyridin-3-yl)-methylamine (1.00 g, 0.00568 mol) and 5-nitro-isochromen-1-one (1.14 g, 0.00568 mol) were suspended in methanol (10 mL) and the suspension was stirred at 60° C. for 3 hours, then the reaction was microwaved at 100 watts at 100° C. for 60 minutes, and then at 120° C. for 30 min. Solid thus formed was filtered out to yield the product as a yellow solid (1.2 g). MS m/z=350.4 (M+H).

Workup

customthe reaction was microwaved at 100 watts at 100° C. for 60 minutes
waitat 120° C. for 30 min
customSolid thus formed
filtrationwas filtered out

Sources & evidence

ORD record: ord-941e7b52dc8d4097a1759eceed356e29
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546579B2

Reaction notes

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