Ammonium Chloride → 1,4-Dichlorophthalazin-6-amine

HRID 1667404Notes

Reaction equation

HRID 1667404 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[C:5]([Cl:15])=[N:4][N:3]=1.[NH4+].[Cl-]>[Fe].CCO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[C:5]([Cl:15])=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 108003021,4-Dichloro-6-nitrophthalazine

Product 1

HCID 584472211,4-Dichlorophthalazin-6-amineYield 30.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1,4-dichloro-6-nitro-phthalazine (1.24 g, 5.09 mmol), EtOH (20 mL), saturated aqueous NH4Cl (20 mL) and iron powder (1.42 g, 25.47 mmol) was heated to reflux for 4 h then concentrated. The residue was taken up in EtOAc washed with saturated aqueous NaHCO3, brine, dried (Na2SO4) and concentrated. Column chromatography (Hexanes/EtOAc) afforded the desired product (0.33 g, 30%) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. concentrationthen concentrated
  4. washwashed with saturated aqueous NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6423bb330234ae291f289a4878fada7
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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