Hydrazine hydrate (1:1) → Methyl 3-{[3-(4-chlorophenyl)-1-(2-hydrazino-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

HRID 714616Notes

Reaction equation

HRID 714616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][CH:19]=3)[C:11](=[O:24])[N:10]([CH2:25][C:26]([O:28]C)=O)[N:9]=2)=[CH:4][CH:3]=1.O.[NH2:31][NH2:32]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][CH:19]=3)[C:11](=[O:24])[N:10]([CH2:25][C:26]([NH:31][NH2:32])=[O:28])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67407710Methyl 3-{[3-(4-chlorophenyl)-1-(2-methoxy-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

Product 1

HCID 69940030Methyl 3-{[3-(4-chlorophenyl)-1-(2-hydrazino-2-oxoethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

172 mg (0.41 mmol) of the compound from Example 15A were suspended in 1 ml of ethanol, and 40 μl (0.83 mmol) of hydrazine hydrate were added. The mixture was heated under reflux for 4 h and then allowed to stand at room temperature for 18 h. The reaction was concentrated under reduced pressure on a rotary evaporator and the residue was dried under high vacuum. This gave 161 mg (94% of theory) of the target compound as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationThe reaction was concentrated under reduced pressure on a rotary evaporator
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-ec80d370e8c44ce6ad8042f05be59681
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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