4-Fluoro-3-nitrobenzotrifluoride → 1-(Tetrahydropyran-4-yl)amino-2-nitro-4-trifluoromethylbenzene

HRID 74150

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>N1C=CC=CC=1>[O:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 98 °C

Procedure

A 3-neck flask (200 mL) was charged with 1-fluoro-2-nitro-4-trifluoromethylbenzene (1.59 g, 7.61 mmol), 4-aminotetrahydropyran (1.00 g, 9.89 mmol), and pyridine (16 mL), and this was stirred at 98° C. for 23 hours. The yellow oil produced was allowed to cool, distilled water (approx. 20 mL) was added with stirring, and the precipitated crystals were filtered off. These were washed with distilled water and dried with heating at reduced pressure to yield the title compound (2.00 g, 90.5% yield) as yellow crystals.

Workup

customThe yellow oil produced
temperatureto cool
distillationdistilled water (approx. 20 mL)
additionwas added
stirringwith stirring
filtrationthe precipitated crystals were filtered off
washThese were washed with distilled water
customdried
temperaturewith heating at reduced pressure

Sources & evidence

ORD record: ord-359360c049ef4f41afd2e711efcfdd3b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829035B2

Linked notes

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