Ammonium Chloride → HCID 43115327, compound

HRID 1817887Notes

Reaction equation

HRID 1817887 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([NH:6][CH2:7][CH:8]2[CH2:10][CH2:9]2)=[C:4]([N+:13]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:6][CH2:7][CH:8]2[CH2:10][CH2:9]2)=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 29274404HCID 29274404, compound

Product 1

HCID 43115327HCID 43115327, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-N-(cyclopropylmethyl)-2-nitroaniline (Step A, 1.7 g, 6.2 mmol), iron (1.7 g, 31.2 mmol) and ammonium chloride (33 mg, 0.62 mmol) in ethanol (18 mL) and water (6 mL) was stirred under reflux for 4 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate (40 mL) and the mixture was washed with water containing aqueous ammonia. The organic layer was separated, dried over sodium sulfate and concentrated to afford the title compound (1.48 g, 98%) as a brown oil.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  5. washthe mixture was washed with water containing aqueous ammonia
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-838f7bde2d70409e82acba3fe952c1ad
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…