Ethanol → 1H-Indazole-1-propanamine, 3-amino-N,N-diethyl-

HRID 484842Notes

Reaction equation

HRID 484842 reaction equation
C(O)C.[CH2:4]([N:6]([CH2:30][CH3:31])[CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([N:19]2C(=O)C3=CC=CC=C3C2=O)=[N:11]1)[CH3:5].O.NN>O>[CH2:30]([N:6]([CH2:4][CH3:5])[CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:19])=[N:11]1)[CH3:31]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 201358851-(3-Diethylaminopropyl)-3-phthalimidoindazole

Product 1

HCID 30288931H-Indazole-1-propanamine, 3-amino-N,N-diethyl-Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 70 ml of ethyl alcohol was added 3.30 g of 1-(3-diethylaminopropyl)-3-phthalimidoindazole. The mixture was added with 2.50 g of 85% hydrazine hydrate under cooling with ice and stirred for 3 hours under cooling with ice. The reaction mixture was filtered and the filtrate was condensed under reduced pressure. The condensed residue was added with 20 ml of water and the reaction product was extracted with chloroform. The chloroform layer was extracted with 2N-hydrochloric acid and the pH of the hydrochloric acid layer was adjusted to 10 with potassium carbonate. The alkali layer was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure to give 1.78 g of 1-(3-diethylaminopropyl)-3-aminoindazole having the following analytical values in a yield of 85%.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. filtrationThe reaction mixture was filtered
  4. customcondensed under reduced pressure
  5. extractionthe reaction product was extracted with chloroform
  6. extractionThe chloroform layer was extracted with 2N-hydrochloric acid
  7. extractionThe alkali layer was extracted with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, and chloroform
  9. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-a8b81b5a852641bf8b23515203e64cae
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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