Ammonium Chloride → HCID 20670051, compound

HRID 380690Notes

Reaction equation

HRID 380690 reaction equation
[Cl:1][C:2]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:22][C:21]1[C:2]([Cl:1])=[C:3]([CH:18]=[CH:19][CH:20]=1)[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 20670035HCID 20670035, compound

Product 1

HCID 20670051HCID 20670051, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of the nitro compound from Example 52 (0.50 g) and ammonium chloride (0.5 g) were dissolved in 50% aqueous ethanol. Iron powder (0.5 g) was added and the mixture stirred at reflux temperature for 3 hr before being cooled and solids removed by filtration. The filtrate was treated with 10% sodium hydroxide solution and the product extracted into ethyl acetate. The organic solution was washed with brine, dried over sodium sulphate (Na2SO4) and concentrated to give a residue which was purified by silica gel chromatography to give the title compound as a white powder (0.45 g).

Workup

  1. temperatureat reflux temperature for 3 hr
  2. temperaturebefore being cooled
  3. customsolids removed by filtration
  4. additionThe filtrate was treated with 10% sodium hydroxide solution
  5. extractionthe product extracted into ethyl acetate
  6. washThe organic solution was washed with brine
  7. dry with materialdried over sodium sulphate (Na2SO4)
  8. concentrationconcentrated
  9. customto give a residue which
  10. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-63e8d089dbf04dbdb8f959faabbed5ed
Source dataset
uspto-grants-2001_10
Patent number
US06303659B2

Reaction notes

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