Ammonium Chloride → HCID 67976218, compound

HRID 706670Notes

Reaction equation

HRID 706670 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:22]=[CH:23][CH:24]=2)[C:18]([O:20][CH3:21])=[O: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:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67976101Methyl 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)benzoate

Product 1

HCID 67976218HCID 67976218, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of methyl 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)benzoate (1.00 g, 2.29 mmol) and MeOH (45 mL) was cooled to 0° C. Zinc dust (0.748 g, 11.4 mmol) was added followed by saturated aqueous NH4Cl (23 mL). The mixture was stirred at 0° C. for 2 hours, then warmed to ambient temperature and stirred for an additional 3 hours. The mixture was diluted with MeOH and filtered. To the filtrate was added saturated aqueous NH4OAc and the mixture was concentrated to remove bulk MeOH. The concentrated mixture was extracted with EtOAc and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, then dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (25 to 100% EtOAc/hexane) to afford 0.398 g (61%) of the title compound as a sticky orange foam.

Workup

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

Sources & evidence

ORD record
ord-50fa0481bf784ac4858f6a48a615bf9f
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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