3-Pyridinecarboxaldehyde → N-(4-(2,4-Difluorophenoxy)phenyl)pyrid-3-ylmethyleneamine

HRID 392399Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

4-(2,4-Difluorophenoxy)aniline (2.21 g, 10.0 mmol) and pyridine-3-carboxaldehyde (1.12 g, 10.5 mmol) were dissolved in anhydrous methanol (35 ml) and the solution was heated at 55° C. for three hours. The solution was cooled and concentrated in vacuo to a residual oil, which was maintained under a 90 μm Hg vacuum for twenty-four hours. N-(4-(2,4-Difluorophenoxy)phenyl)pyrid-3-ylmethyleneamine was obtained in quantitative yield. 1H NMR(400 MHz): 6.83-6.90(1H,m), 6.93-7.00(3H,m), 7.05-7.13(1H,m), 7.21-7.27(2H,m), 7.40(1H,dd, J=8.1, 4.9), 8.27(1H,dd,J=8.1, 1.7), 8.50(1H,s), 8.69(1H,dd,J=4.9, 1.7), 9.00(1H,d,J=1.7); MS(ESI)m/z 311.1([M+H]+,100); Anal. Calcd. for C18H12F2N2O C,69.67; H,3.90; N,9.03. Found: C,69.28; H,3.99; N,8.91.

Workup

temperatureThe solution was cooled
concentrationconcentrated in vacuo to a residual oil, which
temperaturewas maintained under a 90 μm Hg vacuum for twenty-four hours

Sources & evidence

ORD record: ord-75cd74f71b4d475297ebe4cf4c340159
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Reaction notes

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