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

HRID 1293502Notes

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) were dissolved in 50 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 20 hours, 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 (14).

Workup

additionTo this solution, 4 Å molecular sieves were added
additionAfter standing for 20 hours, 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-49dd84d93bd5473a95fb5296b87230d5
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238764B2

Reaction notes

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