Phenylhydrazine hydrochloride → Ethyl 3-(6-oxo-1-phenyl-1,4,5,6-tetrahydropyridazin-3-yl)propanoate

HRID 475483Notes

Reaction equation

HRID 475483 reaction equation
Cl.[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:11]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[O:22]=[C:21]1[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 80592Diethyl 4-oxoheptanedioate

Product 1

HCID 21630617Ethyl 3-(6-oxo-1-phenyl-1,4,5,6-tetrahydropyridazin-3-yl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three neck flask equipped with a Dean-Stark trap, phenylhydrazine hydrochloride and diethyl 4-oxoheptanedioate (1 equiv.) were combined in Toluene (1.15 M). The suspension was stirred 48 h at reflux. The reaction mixture was cooled to rt and concentrated under vacuum to afford the desired material as a brown oil which was used as such in the next step.

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cb8ff5ba9e134da7bb593e0944143d7c
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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