Hydrochloric Acid → 2-(4-(diethylamino)phenyl)-1-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chloride

HRID 2206447Notes

Reaction equation

HRID 2206447 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)[CH3:2].C=O.[ClH:15].[CH2:16](O)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=O)=[CH:23][CH:22]=1>C(#N)C>[Cl-:15].[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:27]([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)=[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N+:30]3=[CH:16]2)=[CH:6][CH:5]=1)[CH3:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 712FormaldehydeHCID 7120N,N-Diethyl-p-phenylenediamineHCID 80559(4-Methoxyphenyl)-2-pyridinylmethanone

Product 1

HCID 783204632-(4-(diethylamino)phenyl)-1-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

was prepared according to general procedure (A), in which freshly distilled 0.12 μl N,N-diethylbenzene-1,4-diamine (0.74 mmol, 1 equiv), 83 μl formalin (0.1.1 mmol, 1.5 equiv), 0.47 mL 3.14 M hydrochloric acid in ethanol (1.5 mmol, 2 equiv) and 0.16 g (4-methoxyphenyl)(pyridin-2-yl)methanone, (0.74 mmol, 1 equiv) were combined in 1.5 mL acetonitrile and maintained at room temperature for 12 hours. The reaction was concentrated in vacuo and dried under high vacuum at 0.2 Torr. The crude material was then triturated with 1.0 mL acetone and diluted with 0.5 mL diethylether. The resulting solution was decanted and the process was repeated an additional two times. The resulting solid was then dissolved in methanol, transferred to a tared vial, concentrated under a stream of nitrogen, and dried under high vacuum at 0.2 Torr for 48 hours to provide 0.27 g, 2-(4-(diethylamino)phenyl)-1-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chloride (0.66 mmol, a 90% yield) as a deliquescent cream colored solid. This material was determined to be the monocationic salt by titration with sodium hydroxide. The material used for fluorescence testing was further purified by recrystallization from acetonitrile and tetrahydrofuran. Crystals used for X-ray diffraction were obtained by layering a concentrated methanolic solution of 2-(4-(diethylamino)phenyl)-1-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chloride with pentane.

Workup

  1. customwas prepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customdried under high vacuum at 0.2 Torr
  4. customThe crude material was then triturated with 1.0 mL acetone
  5. additiondiluted with 0.5 mL diethylether
  6. customThe resulting solution was decanted
  7. dissolutionThe resulting solid was then dissolved in methanol
  8. concentrationconcentrated under a stream of nitrogen
  9. customdried under high vacuum at 0.2 Torr for 48 hours

Sources & evidence

ORD record
ord-447fb2c291944fd89c9d407913e9af77
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

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