2,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one → 2,5,6,11-tetrahydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one

HRID 1414724Notes

Reaction equation

HRID 1414724 reaction equation
[N:1]1[NH:2][C:3](=[O:15])[N:4]2[CH:10]=[CH:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[CH2:6][C:5]=12>[Pd].C(O)(=O)C>[N:1]1[NH:2][C:3](=[O:15])[N:4]2[CH2:10][CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[CH2:6][C:5]=12

Participants

4

Reactant 1

HCID 130667602,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one

Product 1

HCID 214850482,5,6,11-tetrahydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 20 parts of 2,11-dihydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one, 400 volume parts of acetic acid and 15 parts of 5% palladium-on-carbon is hydrogenated at atmospheric pressure and temperature under stirring. After 2600 volume parts of hydrogen is absorbed, the catalyst is removed by filtration. The filtrate is concentrated under reduced pressure and the residue is treated with diethyl ether to give 2,5,6,11-tetrahydro-3H-s-triazolo[3,4-b][3]benzazepin-3-one as crystals. Recrystallization from ethanol gives colorless plates melting at 253° - 261° C.

Workup

  1. customAfter 2600 volume parts of hydrogen is absorbed
  2. customthe catalyst is removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. additionthe residue is treated with diethyl ether

Sources & evidence

ORD record
ord-8a28d2ae969b4584b524966e12487cba
Source dataset
uspto-grants-1977_01
Patent number
US04002638

Reaction notes

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