Hydrazine hydrate (1:1) → 3-Amino-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one

HRID 1632778Notes

Reaction equation

HRID 1632778 reaction equation
C1(=O)[N:5]([CH:6]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]([CH3:18])[CH2:7]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[N:8]([CH3:18])[CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 204423203-Phthalimido-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one

Product 1

HCID 204423323-Amino-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.93 g of 3-phthalimido-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one in 60 ml of absolute ethanol is treated with 0.31 ml of hydrazine hydrate and the reaction mixture is heated to reflux for 1.5 hr. After cooling at room temperature, the solid is removed by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in chloroform and filtered and concentrated again to afford 3-amino-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 1.5 hr
  3. customthe solid is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in chloroform
  6. filtrationfiltered
  7. concentrationconcentrated again

Sources & evidence

ORD record
ord-3b164dd81dd84bd5be119934158384b8
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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