Pyridinium chloride → HCID 86701364, compound

HRID 2179867Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]3[C:14]4[C:19]([C:20]([C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[C:30]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)=[CH:29][CH:28]=5)=[C:21]5[C:26]=3[CH:25]=[CH:24][CH:23]=[CH:22]5)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:10]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>CN1CCCC1=O>[C:37]1([C:30]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:27]([C:20]3[C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]([C:9]4[CH:10]=[C:11]5[C:6]([CH:5]=[CH:4][C:3]([OH:2])=[CH:12]5)=[CH:7][CH:8]=4)=[C:14]4[C:19]=3[CH:18]=[CH:17][CH:16]=[CH:15]4)=[CH:28][CH:29]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 200 °C

Procedure

Under the nitrogen atmosphere, 9-(7-methoxynaphthalen-2-yl)-10-(4-phenylnaphthalen-1-yl)anthracene (16.0 g) as the twentieth intermediate compound, pyridine hydrochloride (17.3 g) and N-methylpyrrolidone (30 ml) were added to a flask and stirred for 8 hours at 200° C. Once the heating is completed, the mixture was cooled to 100° C. or lower. Liquid separation was performed by adding water and toluene. The solvent was distilled off under reduced pressure and the resulting solid was purified by silica gel column chromatography (solvent: toluene) to give 7-(10-(4-phenylnaphthalen-1-yl)anthracen-9-yl)naphthalen-2-ol (15.5 g) as a twenty-first intermediate compound. The scheme is shown in the following “Reaction 33”.

Workup

temperaturethe mixture was cooled to 100° C.
customLiquid separation
additionby adding water and toluene
distillationThe solvent was distilled off under reduced pressure
customthe resulting solid was purified by silica gel column chromatography (solvent: toluene)

Sources & evidence

ORD record: ord-e96d3a8eb50d4555928d49a536b5dc0e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09070885B2

Reaction notes

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