Water → 3-Methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068800Notes

Reaction equation

HRID 1068800 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:28])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1C(=O)C2=CC=CC=C2C1=O.O.NN.O>C(O)C>[NH2:17][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:28])[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 21190184HCID 21190184, compound

Product 1

HCID 211902113-Methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5.99 g (16.0 mmol) of 1,2-dihydro-3-methyl-1-[4-(phthalimido)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one in 150 ml of ethanol was added 2.40 g (48.0 mmol) of hydrazine monohydrate. The mixture was heated for one hour under reflux. After cooling, and the resulting precipitates were filtered off. The filtrate was concentrated to give the residue, water was water, extracted with chloroform (three times). The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 3.17 g of the desired compound (81.1%, pale yellow solid).

Workup

  1. temperatureThe mixture was heated for one hour
  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. extractionextracted with chloroform (three times)
  9. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-295f39645743427d8e5cb3e1410392b9
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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