Sodium Hydroxide → 1,10-Phenanthrolin-5-amine

HRID 341910

Reaction equation

HRID 341910 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]2[C:11]([N:12]=[CH:13][CH:14]=[CH:15]2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-])=O.[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:17]=[C:16]2[C:11]([N:12]=[CH:13][CH:14]=[CH:15]2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 727905-Nitro-1,10-phenanthroline

Product 1

HCID 6069701,10-Phenanthrolin-5-amineYield 66.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

In 3.0 ml of acetic acid was dissolved 1.37 g (5.8 mmol) of 5-nitro-1,10-phenanthroline. A solution prepared by dissolving 1.08 g (4.8 mmol) of stannic chloride (II) dihydrate in 2.2 ml of concentrated hydrochloric acid was added dropwise thereto, followed by stirring at 100° C. for 2 hours. The reaction mixture was made alkaline with a NaOH aqueous solution and extracted with chloroform. After chloroform was distilled off under reduced pressure, a yellow solid was obtained. This was recrystallized from tetrahydrofurane-hexane to obtain 0.75 g (66%) of the desired 5-amino-1,10-phenanthroline (Compound (2)).

Workup

  1. customA solution prepared
  2. additionwas added dropwise
  3. extractionextracted with chloroform
  4. distillationAfter chloroform was distilled off under reduced pressure
  5. customa yellow solid was obtained
  6. customThis was recrystallized from tetrahydrofurane-hexane

Sources & evidence

ORD record
ord-af28943d36054b04a8bec810d584c985
Source dataset
uspto-grants-1999_01
Patent number
US05856479

Linked notes

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