Ammonium Chloride → HCID 23155121, compound

HRID 1912787Notes

Reaction equation

HRID 1912787 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=[O:2].[Cl-].[NH4+]>O1CCOCC1.[Zn]>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([NH:1][OH:2])=[CH:9][CH:8]=2)[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:12]=[CH:11]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 23155053HCID 23155053, compound

Product 1

HCID 23155121HCID 23155121, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

In 3 mL of dioxane, 40 mg (0.167 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine obtained in Step A of Example 1 was dissolved, and 40 mg of zinc powder and 1 mL of a saturated ammonium chloride aqueous solution were added thereto and the mixture solution was vigorously stirred at room temperature for one hour. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with a sodium chloride solution, dried and then concentrated under reduced pressure to obtain a crude product of N-(4-imidazo[4,5-c]pyridine-1-ylphenyl)-hydroxylamine. The product was used in the next reaction without further purification.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a sodium chloride solution
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d530de0f8fd74ac5b83a566d6f5626e9
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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