Hydrochloric Acid → HCID 86670503, compound

HRID 333559Notes

Reaction equation

HRID 333559 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[CH2:18](OC(OCC)OCC)C.[ClH:28]>C(O)=O>[Cl-:28].[CH:1]([N+:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 67256828HCID 67256828, compound

Product 1

HCID 86670503HCID 86670503, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidCatalyst

Procedure

N3-isopropyl-N2-phenylpyridine-2,3-diamine (10 g, 44.0 mmol), triethoxymethane (293 mL, 1760 mmol), formic acid (0.017 mL, 0.440 mmol) and hydrogen chloride (4.24 mL, 44.0 mmol) were mixed together and heated to reflux overnight. The reaction mixture was cooled to room temperature and the precipitate was filtered off. The solid product was collected and washed with hexanes. 1-isopropyl-3-phenyl-3H-imidazo[4,5-b]pyridin-1-ium chloride (8.1 g, 67% yield) was isolated as white crystalline solid after recrystallization from boiling ethanol.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. filtrationthe precipitate was filtered off
  4. customThe solid product was collected
  5. washwashed with hexanes

Sources & evidence

ORD record
ord-46b69413cb374db4a15f6b2008f26144
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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