Ethanol → 6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

HRID 1051271Notes

Reaction equation

[CH3:1][C:2]1[C:3]([N+:23]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[N:7][CH:6]=[CH:5]2.C(O)C.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=3)=[N:7][CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:23]

Participants

Conditions

Temperature: 90 °C

Procedure

6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinoline-1-amine (1.49 g, 4.29 mmol) obtained in Step (1) above was stirred in a solvent of ethanol (10 mL). The reaction solution was added with tin chloride (II) dihydrate (4.06 g, 21.46 mmol), and stirred for about 5 hours at 90° C. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.42 g, 31%).

Workup

washwashed with a saturated aqueous sodium bicarbonate solution and saline
customThe organic layer thus obtained
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c58953cc22b8441388a9dd5c6cb91e2f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388165B2

Reaction notes

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