Hydrazine hydrate (1:1) → 3-Methyl-1-[5-(amino)pentyl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068797Notes

Reaction equation

HRID 1068797 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:29])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O.O.NN>C(O)C>[NH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:8]1[C:9]2[N:5]3[C:4](=[N:3][C:2]([CH3:1])=[C:6]3[C:7]1=[O:29])[CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21190142HCID 21190142, compound

Product 1

HCID 211901113-Methyl-1-[5-(amino)pentyl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6.26 g (16.1 mmol) of 1,2-dihydro-3-methyl-1-[5-(phthalimido)pentan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one in 120 ml of ethanol was added 2.42 g (48.3 mmol) of hydrazine monohydrate. The mixture was heated for two hours under reflux. After cooling, the resulting precipitates were filtered off. The filtrate was concentrated to give the residue, water was added, extracted with chloroform (three times). The extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 3.31 g of the desired compound (79.6%, pale yellow solid substance).

Workup

  1. temperatureThe mixture was heated for two hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated
  7. customto give the residue, water
  8. additionwas added
  9. extractionextracted with chloroform (three times)
  10. dry with materialThe extract was dried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4994e7572e0b4c93b20303a2ecfd49d8
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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