2-Fluoroaniline → 2-[1-(2,4,6-Trimethylphenylimino) ethyl]-6-[1-(2-fluorophenylimino)ethyl]pyridine

HRID 49751

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=O)[CH3:20])[N:14]=1)[CH3:12].[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[N:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[F:22])[CH3:20])[N:14]=1)[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

Monoimine (1, 1.0 g, 3.57 mmol) and 2-fluoroaniline (398 mg, 3.57 mmol) (ex. Aldrich) were dissolved in 50 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 20 hrs., with addition of more molecular sieves, the mixture was filtered. The solvent was removed in vacuum and the oily residue was warmed in ethanol (50° C.). The yellow solid, which precipitated after cooling at −20° C., was filtered off and dried in vacuo. Yield 300 mg (23%) of mixed diimine (4).

Workup

additionTo this solution, 4 Å molecular sieves were added
addition, with addition of more molecular sieves
filtrationthe mixture was filtered
customThe solvent was removed in vacuum
customThe yellow solid, which precipitated
temperatureafter cooling at −20° C.
filtrationwas filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-5cf68a390d7c4ef1aa9f36af3a6e1ed9
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710006B2

Linked notes

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