Ammonium Chloride → HCID 67976137, compound

HRID 706683Notes

Reaction equation

HRID 706683 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[N:3]=1.[NH4+].[Cl-]>CO.[Zn]>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]=[N:3][N:4]2[CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67976383HCID 67976383, compound

Product 1

HCID 67976137HCID 67976137, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A slurry of 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)benzonitrile (0.200 g, 0.495 mmol) and MeOH (10.0 mL) was cooled to 0° C., then Zn dust (0.162 g, 2.47 mmol) was added followed by saturated aqueous NH4Cl (10 mL). The mixture was stirred at 0° C. for 1 hour, then warmed to ambient temperature and stirred overnight. The mixture was diluted with MeOH and filtered. The solid was washed with CH2Cl2 and MeOH. To the filtrate was added saturated aqueous NH4OAc and the mixture was concentrated to remove bulk MeOH. The mixture was then extracted with EtOAc, and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (25 to 100% EtOAc/hexane) to afford 0.090 g (73%) of the desired product as an orange oil.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred overnight
  3. filtrationfiltered
  4. washThe solid was washed with CH2Cl2 and MeOH
  5. additionTo the filtrate was added saturated aqueous NH4OAc
  6. concentrationthe mixture was concentrated
  7. customto remove bulk MeOH
  8. extractionThe mixture was then extracted with EtOAc
  9. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was purified by column chromatography (25 to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-324c0ad355e84c9e8b63c969f75a512d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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