Hydrazine hydrate (1:1) → (S)-5-methyl-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

HRID 1619941Notes

Reaction equation

HRID 1619941 reaction equation
[CH3:1][C@H:2]([C:7](=O)[C:8]1[CH:22]=[CH:21][C:11]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:10]=2[CH:9]=1)[CH2:3][C:4](O)=[O:5].O.[NH2:25][NH2:26]>C(O)C>[CH3:1][C@@H:2]1[C:7]([C:8]2[CH:22]=[CH:21][C:11]3[N:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:14][C:10]=3[CH:9]=2)=[N:26][NH:25][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67462340(S)-3-methyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

Product 1

HCID 54591647(S)-5-methyl-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

177 mg (572 μmol) (S)-3-methyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid are combined with 10 ml of ethanol and 350 μl (7050 μmol) hydrazine hydrate. The reaction mixture is refluxed for 3 h. The solvent is eliminated by rotary evaporation in vacuo and the residue is separated through silica gel (eluant cyclohexane/EA).

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. customThe solvent is eliminated by rotary evaporation in vacuo
  3. customthe residue is separated through silica gel (eluant cyclohexane/EA)

Sources & evidence

ORD record
ord-b68d4353ef194ccf8b3f3df573c68784
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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