Hydrazine hydrate (1:1) → HCID 19008993, compound

HRID 1742284Notes

Reaction equation

HRID 1742284 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]3[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:17][N:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=34)=[N:9]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[N:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19009015HCID 19009015, compound

Product 1

HCID 19008993HCID 19008993, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[2-(2-phthalimidoethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.2 g), hydrazine monohydrate (2 ml), and ethanol (100 ml) was stirred for 1 hour under reflux. After being cooled to room temperature, the reaction mixture was concentrated, and the residue was partitioned between chloroform and water. The organic layer was separated, and extracted with 10% hydrochloric acid. The aqueous layer was washed twice with chloroform, neutralized with sodium hydroxide, and extracted three times with chloroform. The combined organic layers were washed with water and sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated to give 3-[2-(2-aminoethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.5 g). An analytical sample was prepared by recrystallization from ethyl acetate.

Workup

  1. temperatureunder reflux
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was partitioned between chloroform and water
  4. customThe organic layer was separated
  5. extractionextracted with 10% hydrochloric acid
  6. washThe aqueous layer was washed twice with chloroform
  7. extractionextracted three times with chloroform
  8. washThe combined organic layers were washed with water and sodium chloride aqueous solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7d746725ac5940ad9fac8f48aff849cc
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

Loading…