Hydrazine hydrate (1:1) → cis-1-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine

HRID 1639768Notes

Reaction equation

HRID 1639768 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@H:11]2[CH2:13][C@H:12]2[CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)=[N:3]1.O.NN>C(O)C>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@H:11]2[CH2:13][C@H:12]2[CH2:14][NH2:15])=[N:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66720712HCID 66720712, compound

Product 1

HCID 66720689cis-1-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A crudely purified product of cis-2-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione was dissolved in ethanol (6.5 mL), and hydrazine monohydrate (3 mL) was added. The mixture was heated under reflux for 20 min. The solvent was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 min
  3. customThe solvent was evaporated under reduced pressure
  4. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f66e6b321fc1401fad3f65b85370967c
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…