Ammonium Chloride → HCID 21877792, compound

HRID 896164Notes

Reaction equation

HRID 896164 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): [M+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-cb5f8cb22b6548f3a431e3e190571ddd
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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