Ammonium Chloride → HCID 90029042, compound

HRID 2200160Notes

Reaction equation

HRID 2200160 reaction equation
[F:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[NH:4][CH:3]=1.[Cl-].[NH4+]>CO.[Zn]>[F:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 11030408HCID 11030408, compound

Product 1

HCID 90029042HCID 90029042, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Add zinc powder (387 mg, 5 mmol) portionwise to a solution of 3-fluoro-5-nitro-1H-indole (360 mg, 2 mmol) in methanol (10 mL). Then add dropwise 15.5% ammonium chloride solution (10 mL, 20 mmol), stir the reaction at ambient temperature for 5 hrs. Filter, dilute the filtrate with water (50 mL), extract with ethyl acetate (50 mL×2), wash with brine (50 mL×2), dry over anhydrous sodium sulfate. Concentrate under reduced pressure to give the crude product. Purify by flash chromatography (silica gel, EtOAc:PE=1:3) to yield the title compound (150 mg, 50%). MS: (M+1): 151.2.

Workup

  1. customthe reaction at ambient temperature for 5 hrs
  2. filtrationFilter
  3. additiondilute the filtrate with water (50 mL)
  4. extractionextract with ethyl acetate (50 mL×2)
  5. washwash with brine (50 mL×2)
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationConcentrate under reduced pressure
  8. customto give the crude product
  9. customPurify by flash chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-8a33fab372b346118cea49f187a44ae4
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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