Ammonium Chloride → 6(5h)-Phenanthridinone, 2-amino-

HRID 1016481Notes

Reaction equation

HRID 1016481 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1)([O-])=O.[Cl-].[NH4+]>CN(C=O)C.[Fe]>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 1571802-Nitro-6(5H)-phenanthridinone

Product 1

HCID 2706686(5h)-Phenanthridinone, 2-amino-Yield 101.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-nitro-6(5H)-phenanthridinone (3.8 g, 0.016 mol) in DMF (200 mL) was added an ammonium chloride solution (3%, 200 mL), followed by the addition of iron powder (22 g). The reaction mixture was stirred at 100° C. for 1 hr. The residue was removed by filtration, and the filtrate was made acidic by adding dilute HCl (25%, 20 mL). A solid separated from the solution and was filtered and washed thoroughly with cold water to remove acidic impurities. The solid was then dried under vacuum, to give hydrochloride salt of 2-amino-6(5H)-phenanthridinone (3.4 g, 89%).

Workup

  1. customThe residue was removed by filtration
  2. additionby adding dilute HCl (25%, 20 mL)
  3. customA solid separated from the solution
  4. filtrationwas filtered
  5. washwashed thoroughly with cold water
  6. customto remove acidic impurities
  7. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-899a32aea04c45eaa54f95ebbbf3003d
Source dataset
uspto-grants-2002_11
Patent number
US06476048B1

Reaction notes

Loading…