Ammonium Chloride → HCID 21104298, compound

HRID 1354046Notes

Reaction equation

HRID 1354046 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6]1.[Cl-].[NH4+]>C(O)C.C1COCC1.O.[Fe]>[Cl:1][C:2]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21104297HCID 21104297, compound

Product 1

HCID 21104298HCID 21104298, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of compound II (6.9 g) in ethanol/THF/water (ratio 40:20:10) was added ammonium chloride (3.3 g) and powdered iron (3.4 g). This mixture was heated to reflux for 5 h. The hot mixture was then filtered through Celite and concentrated. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3 solution followed by water and then brine. The solution was dried over magnesium sulfate and concentrated to afford compound III as an off-white solid (5.6 g).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe hot mixture was then filtered through Celite
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated NaHCO3 solution
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a5655081d23442d4ab104fc073c95192
Source dataset
uspto-grants-2007_05
Patent number
US07223761B2

Reaction notes

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