2-Pyridinecarboxaldehyde → Bis-{-4-(pyridin-2-yl-methyleneamino)-3,5-diisopropylphenyl}-methane

HRID 17788Notes

Reaction equation

[CH2:1]([C:15]1[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:18]([NH2:19])=[C:17]([CH:25]([CH3:27])[CH3:26])[CH:16]=1)[C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]=O>C(O)C.C(O)=O>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]=[N:19][C:18]1[C:20]([CH:22]([CH3:24])[CH3:23])=[CH:21][C:15]([CH2:1][C:2]2[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[C:5]([N:6]=[CH:34][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=2)=[CH:16][C:17]=1[CH:25]([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of 2b (1.60 g, 4.37 mmol) in absolute ethanol (10 ml) was added 2-pyridinecarboxaldehyde (1.24 ml, 13.11 mmol, 3 eq.) and two drops of formic acid. The mixture was stirred at 45° C. overnight. On cooling to room temperature the suspension was filtered, washed with cold ethanol and dried under reduced pressure to afford 18a as a yellow solid (1.68 g, 49%).

Workup

temperatureOn cooling to room temperature the suspension
filtrationwas filtered
washwashed with cold ethanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-2b2c2a3f6a9040419cf2c4e5b43e5e76
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741240B2

Reaction notes

Loading…