Ammonium Chloride → HCID 59843209, compound

HRID 2196570Notes

Reaction equation

HRID 2196570 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([N+:18]([O-])=O)[C:11]=2[N:10]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([NH2:18])[C:11]=2[N:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 59843298HCID 59843298, compound

Product 1

HCID 59843209HCID 59843209, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 163 (0.620 g, 2.303 mmol), ammonium chloride (0.105 g, 1.957 mmol) and iron (0.643 g, 11.51 mmol) in ethanol (20 ml) and water (4.00 ml) was heated at reflux for 2 hours. The reaction mixture was cooled and filtered through Celite and the filtrate was taken to dryness, H20 was added and the material extracted with ethyl acetate. The EtOAc extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give crude 164 (0.5245 g, 2.192 mmol, 95% yield) as brown solid. LRMS (ESI): (calc.) 239.3 (found) 240.2 (MH)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite
  5. additionwas added
  6. extractionthe material extracted with ethyl acetate
  7. washThe EtOAc extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9ffdaec9c8824469bd5a6ecc75810377
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

Loading…