Ammonium Chloride → HCID 67976165, compound

HRID 706699Notes

Reaction equation

HRID 706699 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[C:16](=[O:22])[N:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[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[C:16](=[O:22])[N:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67976294HCID 67976294, compound

Product 1

HCID 67976165HCID 67976165, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

3-((3-Iodo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (0.26 g, 0.63 mmol) was added to MeOH (6 mL) and cooled to 0° C. Zinc (0.21 g, 3.2 mmol) was added to the reaction mixture. Saturated aqueous NH4Cl (6 mL) was added drop-wise and the reaction mixture was stirred for 90 minutes at ambient temperature. The reaction was diluted with MeOH (50 mL), stirred for 5 minutes and filtered. The filtrate was diluted with saturated NH4OAc and the MeOH was removed under vacuum. The aqueous mixture was extracted with CHCl3. The organic layer was washed with brine, dried over MgSO4 and concentrated to provide 3-((4-amino-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (0.12 g, 71% yield) as a solid.

Workup

  1. stirringstirred for 5 minutes
  2. filtrationfiltered
  3. additionThe filtrate was diluted with saturated NH4OAc
  4. customthe MeOH was removed under vacuum
  5. extractionThe aqueous mixture was extracted with CHCl3
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-675e67a05f8244a4a26d5a3bbd0cfdaf
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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