2-Naphthalenecarboxaldehyde → HCID 67050819, compound

HRID 888704Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)(=O)[CH3:14].[OH-].[Na+].CO.C([O-])(=O)C.[NH4+:30].[I-].[Br:32][C:33]1[CH:47]=[CH:46][C:36]([C:37](=O)[CH2:38][N+]2C=CC=CC=2)=[CH:35][CH:34]=1>CO>[Br:32][C:33]1[CH:47]=[CH:46][C:36]([C:37]2[N:30]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH:38]=2)=[CH:35][CH:34]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Subsequently, 6.0 g of 2-naphthoaldehyde, 4.7 g of 2-acetylpyridine, and 40 ml of methanol were added and the whole was cooled to −5° C. under stirring. 62 ml of a 3 wt % NaOH/methanol solution was added dropwise thereto and the whole was stirred at −5° C. for 2 hours. Then, the reaction was further carried out at the same temperature for 2 days. 37.0 g of ammonium acetate, 15.5 g of the above 4-bromophenacylpyridinium iodide, and 100 ml of methanol were added to the reaction solution and the whole was stirred at 55° C. for 2 days. After cooling to room temperature, the resulting crude product was collected by filtration, washed with methanol, and then dried under reduced pressure at 70° C. for 12 hours to obtain 3.8 g (yield 23%) of 6-(4-bromophenyl)-4-(naphthalen-2-yl)-[2,2′]bipyridine as a gray powder.

Workup

stirringthe whole was stirred at −5° C. for 2 hours
stirringthe whole was stirred at 55° C. for 2 days
temperatureAfter cooling to room temperature
filtrationthe resulting crude product was collected by filtration
washwashed with methanol
customdried under reduced pressure at 70° C. for 12 hours

Sources & evidence

ORD record: ord-799e27180346445d89d812bd797cbb26
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252431B2

Reaction notes

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