Hydrazine hydrate (1:1) → 3-(1-Methylethyl)-1,2,4-oxadiazole-5-methanamine

HRID 385771Notes

Reaction equation

HRID 385771 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[O:6][N:5]=1)([CH3:3])[CH3:2].O.NN>C(O)C>[CH:1]([C:4]1[N:8]=[C:7]([CH2:9][NH2:10])[O:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 363075112-((3-Isopropyl-1,2,4-oxadiazol-5-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 280631563-(1-Methylethyl)-1,2,4-oxadiazole-5-methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a vigorously stirred suspension of compound 2-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione (79 g, 0.29 mol) in ethanol (500 mL), hydrazine hydrate (16 g, 0.32 mol) was added. After the precipitate was completely dissolved, the reaction mixture was heated to reflux for 4 h. The precipitate was removed by filtration. The mother liquor was evaporated. The residue was dissolved in ether (200 mL). The precipitate was removed by filtration. The filtrate was evaporated. The residue was redistilled under high vacuum collecting the fraction boiling at 62-65° C./0.02 mmHg to yield the title compound.

Workup

  1. additionwas added
  2. dissolutionAfter the precipitate was completely dissolved
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 4 h
  5. customThe precipitate was removed by filtration
  6. customThe mother liquor was evaporated
  7. dissolutionThe residue was dissolved in ether (200 mL)
  8. customThe precipitate was removed by filtration
  9. customThe filtrate was evaporated
  10. distillationThe residue was redistilled under high vacuum
  11. customcollecting the fraction boiling at 62-65° C./0.02 mmHg

Sources & evidence

ORD record
ord-5dbf3e6c4e90493eac999aa7112cce70
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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