2-Ethylaniline → N,N′-(2,6-Pyridinediyldiethylidyne)bis[2-ethylbenzenamine]

HRID 2297072Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[CH2:13]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17])[CH3:14]>C(O)=O.CO>[CH2:13]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[N:17]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[CH2:13][CH3:14])[CH3:11])[N:5]=1)[CH3:2])[CH3:14]

Participants

Conditions

Temperature: 50 °C

Procedure

One g of 2,6-diacetylpyridine and 3.0 ml of 2-ethylaniline were added to a round-bottom flask with 30 ml of methanol. A stirbar and 5 drops of 97% formic acid were added, and the flask was sealed and the solution was stirred for 24 hours at 50° C. The flask was then cooled to room temperature and placed in a freezer at −30° C. After 1 day, yellow crystals had formed. The crystals were isolated by filtration and identified by 1H NMR as the desired product (1.25 g, 55.2%). 1H NMR (CDCl3): δ8.38(d, 2, Hpyr), 7.86(t, 1, Hpyr), 7.20(m, 4, Haryl), 7.07(t, 2, Haryl), 6.65(d, 2, Haryl), 2.49(q, 4, Hbenzyl), 2.35(s, 6, N—C—CH3), 1.14(t, 6, CH2CH3).

Workup

customthe flask was sealed
temperatureThe flask was then cooled to room temperature
customplaced in a freezer at −30° C
waitAfter 1 day
customyellow crystals had formed
customThe crystals were isolated by filtration

Sources & evidence

ORD record: ord-5dc372b9f2ce465f94921442cd20cf07
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489497B1

Reaction notes

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