2-Naphthalenecarboxaldehyde → HCID 67050819, compound

HRID 1618821Notes

Reaction equation

HRID 1618821 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

7

Reactant 5

HCID 62012-NaphthalenecarboxaldehydeHCID 142862-AcetylpyridineHCID 517165Ammonium AcetateHCID 135522811-[2-(4-Bromophenyl)-2-oxoethyl]pyridin-1-ium iodideHCID 23721981Sodium hydroxide methanol

Product 1

HCID 67050819HCID 67050819, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-5 °C

Procedure

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

Workup

  1. stirringthe mixture was stirred at −5° C. for 2 hours
  2. stirringthe mixture was stirred at 55° C. for 2 days
  3. temperatureAfter cooling to room temperature
  4. filtrationthe resulting crude product was collected by filtration
  5. washwashed with methanol
  6. customDrying
  7. waitwas performed under reduced pressure at 70° C. for 12 hours

Sources & evidence

ORD record
ord-8744d86a2d2d407f8d60f4b0978a4aa2
Source dataset
uspto-grants-2014_07
Patent number
US08771841B2

Reaction notes

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