Trifluoroacetic acid → 4-(6-Methyl-5-nitroisoquinolin-1-ylamino)benzonitrile

HRID 1042250Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl[C:11]1[C:20]2[C:15](=[C:16]([N+:22]([O-:24])=[O:23])[C:17]([CH3:21])=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1.C(O)(C(F)(F)F)=O>C(O)(C)C>[CH3:21][C:17]1[C:16]([N+:22]([O-:24])=[O:23])=[C:15]2[C:20](=[CH:19][CH:18]=1)[C:11]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[N:12][CH:13]=[CH:14]2

Participants

Conditions

Temperature: 22 °C

Procedure

A mixture of 4-aminobenzonitrile (4.0 g, 34 mmol), isopropanol (50 mL) and 1-chloro-6-methyl-5-nitroisoquinoline (5.0 g, 22 mmol) was stirred at RT (22° C.) and treated with TFA (5.0 mL, 67 mmol). The reaction mixture was stirred at 80° C. for 17 h, and allowed to cool to RT. The thick slurry was diluted with isopropanol (100 mL) and the solid precipitate was collected by suction filtration. The solid was washed with saturated NaHCO3 (2×100 mL), water (50 mL), Et2O (50 mL), and hexane (100 mL) and dried in a vacuum oven at 70° C. overnight to provide 4-(6-methyl-5-nitroisoquinolin-1-ylamino)benzonitrile (6.0 g, 88% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 305 [M+H]+.

Workup

stirringThe reaction mixture was stirred at 80° C. for 17 h
temperatureto cool to RT
filtrationthe solid precipitate was collected by suction filtration
washThe solid was washed with saturated NaHCO3 (2×100 mL), water (50 mL), Et2O (50 mL), and hexane (100 mL)
customdried in a vacuum oven at 70° C. overnight

Sources & evidence

ORD record: ord-8eced44c16ff49e7acf40aea4d16f296
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557830B2

Reaction notes

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