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

HRID 466530

Reaction equation

HRID 466530 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.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[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 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 727905-Nitro-1,10-phenanthroline

Product 1

HCID 6069701,10-Phenanthrolin-5-amineYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A magnetically stirred solution of 5nitro-1, 10-phenanthroline (2,.01 g, 8.93 mmol) and tin(II) chloride dihydrate (6.05 g, 26.81 mmol) was heated to reflux for 3 h in ethanol (100 mL) and then concentrated in vacuo to give a viscous residue. The residue was treated with concentrated NaOH and then extracted with CHCl3 (3×50 mL). The organic layer was separated, washed with water (2×50 mL) and brine (1×50 mL), dried over anhydrous sodium sulfate, and then concentrated in vacuo to afford 1.08 g (62%) of the amine as a tan solid: m.p. 255-258 C; MS(fab):m/e 196 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a viscous residue
  3. extractionextracted with CHCl3 (3×50 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×50 mL) and brine (1×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f4836717b7c4935b2c12884dda28557
Source dataset
uspto-grants-1992_10
Patent number
US05157032

Linked notes

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