p-Fluoronitrobenzene → 2-[2-(4-Nitroanilino)ethyl]pyridine

HRID 33088

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 60 °C

Procedure

2 g of 4-fluoronitrobenzene, 2.07 g of 2-(2-aminoethyl)pyridine, and 2.35 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 18 hours and, after cooling to room temperature, was then poured into a water+ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 3.3 g of N-(4-nitrophenyl)-N-(2-pyrid-2-ylethyl)amine (5) were obtained.

Workup

temperatureafter cooling to room temperature
customThe yellow precipitate formed
filtrationwas filtered off
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-47aeb07bfb9d4ffcbb19763c34e2f767
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429278B2

Linked notes

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