Hydrazine hydrate (1:1) → Azafluorene

HRID 1935323Notes

Reaction equation

HRID 1935323 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13](=O)[C:2]=12.O.NN>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:13][C:2]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 426139H-Indeno(2,1-b)pyridin-9-one

Product 1

HCID 12226515Azafluorene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

Indeno[2,1-b]pyridin-9-one (525 mg, 2.90 mmol), 92 (J. Org. Chem. 51, 2021 (1986)) and 4.5 mL of hydrazine hydrate were combined in a sealed tube and warmed to 180° C. for 16 hours. The resulting mixture was diluted with chloroform and the layers seperated. The organics were dried over sodium sulfate, filtered, and evaporated to dryness. The resulting oil was purified by chromatography on silica gel eluted with 95:5, 93:7, and 90:10 of methylene chloride:ethyl ether. The product fractions were evaporated to dryness to yield the title compound as a yellow solid.

Workup

  1. customthe layers seperated
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting oil was purified by chromatography on silica gel
  6. washeluted with 95:5, 93:7, and 90:10 of methylene chloride
  7. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-6b8b5bdc8ca24d459d089b19348a7da2
Source dataset
uspto-grants-2002_05
Patent number
US06387893B1

Reaction notes

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