Hydrochloric Acid → HCID 69211755, compound

HRID 2218421Notes

Reaction equation

HRID 2218421 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1.Cl>CO.[Fe]>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574826706-Bromo-7-methyl-2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 69211755HCID 69211755, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

6-Bromo-7-methyl-2-(4-nitrophenyl)-1H-imidazo[4,5-b]pyridine (Example 259) (0.11 g, 0.34 mmol) was dissolved in methanol (15 ml) and iron powder (0.097 g, 1.70 mmol) was added. Conc. HCl (1.8 ml) was added dropwise over 15 min. and the reaction mixture was stirred at room temperature for 2 h. Methanol was partly removed by evaporation, after which water and ammonia were added. The aqueous phase was extracted with CHCl3, dried (Na2SO4), filtered and evaporated to yield the product (81.2 mg, 78%).

Workup

  1. customMethanol was partly removed by evaporation
  2. additionafter which water and ammonia were added
  3. extractionThe aqueous phase was extracted with CHCl3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ad39c1955ecb4b0391e3b8152c960b74
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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