Hydrochloric Acid → HCID 178462804, compound

HRID 333552Notes

Reaction equation

HRID 333552 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)C.[ClH:17].C(O[CH2:26][CH3:27])(OCC)OCC>C(O)=O>[Cl:17][N+:3]1([CH2:26][CH3:27])[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH-:1]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 70665410HCID 70665410, compound

Product 1

HCID 178462804HCID 178462804, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N2-ethyl-N3-phenylpyridine-2,3-diamine (8.5 g, 40 mmol), concentrated HCl (6 mL), and 4 mL of formic acid were added to the triethyl orthoformate (376 mL). The reaction was refluxed overnight. After it cooled to room temperature, the beige solid was collected by filtration. The solid was further purified by recrystallizing from ethanol to give 3-chloro-3-ethyl-1-phenyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-3-ium-2-ide (9.4 g, 91% yield).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. filtrationthe beige solid was collected by filtration
  3. customThe solid was further purified
  4. customby recrystallizing from ethanol

Sources & evidence

ORD record
ord-e6aa036cc27a441ca968d25f2050ce80
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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