Hydrazine hydrate (1:1) → 1-Aminopropyl-3-phenyl-5-chloroindazole

HRID 1730947Notes

Reaction equation

HRID 1730947 reaction equation
C1(=O)[N:5]([CH:6]([C:9]2[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:12][NH:13]3)[CH2:7][CH3:8])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH:6]([C:9]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[N:12][NH:13]2)[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 681394741-Phthalimidopropyl-3-phenyl-5-chloroindazole

Product 1

HCID 681391111-Aminopropyl-3-phenyl-5-chloroindazoleYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Phthalimidopropyl-3-phenyl-5-chloroindazole (8.3 g) and hydrazine hydrate (2.0 g) were added to ethanol (150 ml) followed by heating under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure and to the residue were added benzene (150 ml) and 10% aqueous sodium hydroxide solution (200 ml) followed by stirring at room temperature for 1 hour. The organic layer was separated from the mixture and it was washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 5.5 g of 1-aminopropyl-3-phenyl-5-chloroindazole as an oily product. The product was treated with ether-hydrochloric acid to form its hydrochloride. After recrystallization from ethanol-ether, the product had a melting point between 163°-164° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  4. additionwere added benzene (150 ml) and 10% aqueous sodium hydroxide solution (200 ml)
  5. customThe organic layer was separated from the mixture and it
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4d37affc84a4009b0504e3a07fdccf7
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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