3-(Trifluoromethyl)aniline → 6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine

HRID 1042252Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1>C(O)(C)C>[CH3:12][C:8]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=1)=[N:3][CH:4]=[CH:5]2

Participants

Conditions

Temperature: 180 °C

Procedure

1-Chloro-6-methyl-5-nitroisoquinoline (0.25 g, 1.1 mmol) and 3-(trifluoromethyl)benzenamine (0.17 mL, 1.3 mmol) were added to a microwave tube containing 3 mL of isopropanol. The tube was capped and heated at 180° C. for 1500 seconds. The volatiles were removed in vacuo. The residue was taken up in DCM and washed with saturated NaHCO3. The organic layer was dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes to give the product as an orange solid (0.31 g, 79%). MS (M+H)+348.

Workup

customThe tube was capped
customThe volatiles were removed in vacuo
washwashed with saturated NaHCO3
dry with materialThe organic layer was dried with sodium sulfate
custompurified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes

Sources & evidence

ORD record: ord-43e3276e1c7e41159343aece02cb4056
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557830B2

Reaction notes

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