Ammonium Chloride → HCID 21877792, compound

HRID 1991300Notes

Reaction equation

HRID 1991300 reaction equation
[Cl-].[NH4+].[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([F:13])[C:5]=1[N:14]1[CH2:18][CH:17]=[CH:16][CH2:15]1>CCO.O.[Fe]>[N:14]1([C:5]2[C:4]([F:3])=[CH:9][C:8]([NH2:10])=[CH:7][C:6]=2[F:13])[CH2:18][CH:17]=[CH:16][CH2:15]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21878050HCID 21878050, compound

Product 1

HCID 21877792HCID 21877792, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Ammonium chloride (1.18 g, 22.1 mmol) is added to a mixture of 1-(2,6-difluoro-4-nitrophenyl)-2,5-dihydro-1H-pyrrole (Step 1, 0.5 g, 2.21 mmol) dissolved in EtOH/water (2:1, 18.0 mL) and heated to reflux. Iron powder (0.37 g, 6.63 mmol) is added in portions over one hour. After refluxing for another 45 min, the reaction mixture is cooled, filtered, and extracted three times with dichloromethane. The organic layers are washed with saline, dried (MgSO4) and concentrated to provide the title compound (0.43 g, >95%), MS (m/z): [N+H]+=197; 1H NMR (300 MHz, CDCl3): δ 3.63 (bs, 2H), 4.10 (s, 4H), 5.84 (s, 2H), 6.17 (d, 2H).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for another 45 min
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. extractionextracted three times with dichloromethane
  6. washThe organic layers are washed with saline
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-070b050aec064c09a2acb47d54d7d771
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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