Hydrazine hydrate (1:1) → 1,10-Phenanthrolin-5-amine

HRID 2218490Notes

Reaction equation

HRID 2218490 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.NN>CCO.[Pd]>[N:9]1[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:17]=[C:4]([NH2:1])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 727905-Nitro-1,10-phenanthroline2×

Product 1

HCID 6069701,10-Phenanthrolin-5-amineYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

This compound was synthesized by the reduction of 5-nitro-1,10-phenanthroline. The procedure was manipulated under argon. To a suspension of 5-nitro-1,10-phenanthroline (2.06 g, 9.0 mmol) and 10% Pd/C (0.280 g) in 90 ml of 95% EtOH, hydrazine hydrate (2.0 ml, 42 mmol) was added dropwise. The mixture was heated for 3 h at 70° C. and then filtered hot through a glass-fiber filter to remove the catalyst. The yellow solution was concentrated to 25 ml and left at 4° C. for 24 hours. The precipitate was filtered off, washed with cold Et2O, and dried under vacuum for 24 hours to give 1.425 g of product (81%). 1H-NMR (DMSO-d6): δ=9.08 (m, 1H), 8.71 (m, 2H), 8.06 (m, 1H), 7.75 (q, 1H), 7.52 (q, 1H), 6.90 (s, 1H), 6.17 ppm (d, NH2). 13C-NMR (DMSO-d6): δ=149.3, 146.2, 144.8, 142.7, 140.5, 132.7, 130.8, 123.2, 122.0, 101.8 ppm.

Workup

  1. additionwas added dropwise
  2. filtrationfiltered hot through a glass-fiber
  3. filtrationfilter
  4. customto remove the catalyst
  5. concentrationThe yellow solution was concentrated to 25 ml
  6. filtrationThe precipitate was filtered off
  7. washwashed with cold Et2O
  8. customdried under vacuum for 24 hours

Sources & evidence

ORD record
ord-3f9d2c4c837e436bb23c843c026b0826
Source dataset
uspto-grants-2008_08
Patent number
US07411053B2

Reaction notes

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