Ammonium Chloride → HCID 86678204, compound

HRID 1747553Notes

Reaction equation

HRID 1747553 reaction equation
[Cl:1][C:2]1[C:3]([O:15][CH:16]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:17]([F:20])([F:19])[F:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([N+:12]([O-])=O)=[CH:7][CH:6]=2.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([O:15][CH:16]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:17]([F:19])([F:20])[F:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86678203HCID 86678203, compound

Product 1

HCID 86678204HCID 86678204, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a mixed solvent of ethanol (19.5 mL) and water (9.75 mL) was dissolved 3-chloro-6-nitro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy)quinoxaline (975 mg, 2.53 mmol) obtained in Step 2. To the solution were added iron (0) (425 mg, 7.60 mmol) and ammonium chloride (68.0 mg, 1.27 mmol) and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was filtered through Celite and the filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 0/1) to give 3-chloro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline-6-amine (555 mg, 62% yield).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washWashing with saturated brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 0/1)

Sources & evidence

ORD record
ord-d776bc961e68409b983d0dda346cac1d
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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