N-methyl-2-pyrrolidone → HCID 86701347, compound

HRID 2179848Notes

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

Participants

Conditions

Temperature: 200 °C

Procedure

Under the nitrogen atmosphere, 9-(7-methoxynaphthalen-2-yl)-10-(naphthalen-1-yl)anthracene (17.5) as the third intermediate compound, pyridine hydrochloride (22.0 g) and N-methylpyrrolidone (35 ml) were added to a flask and stirred for 6.5 hours at 200° C. Once the heating is completed, the reaction solution was cooled to 100° C. or less, added with water, and the precipitated solid was collected by suction filtration. The crude product obtained was purified by silica gel column chromatography (solvent: toluene) to give 7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalene-2-ol (16.0 g) as a fourth intermediate compound. The scheme is shown in the following “Reaction 5”.

Workup

temperaturethe reaction solution was cooled to 100° C. or less
filtrationthe precipitated solid was collected by suction filtration
customThe crude product obtained
customwas purified by silica gel column chromatography (solvent: toluene)

Sources & evidence

ORD record: ord-81a4a573e77b4b4b868c7e5d2172eb4d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09070885B2

Reaction notes

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