Hydrazine hydrate (1:1) → 6-[4-(3-Chloro-propoxy)-phenyl]-4,5-dihydro-2H-pyridazin-3-one

HRID 2042626Notes

Reaction equation

HRID 2042626 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][Cl:19])=[CH:11][CH:10]=1)=O)C.O.[NH2:22][NH2:23]>C(O)(C)C>[Cl:19][CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[CH2:6][CH2:5][C:4](=[O:3])[NH:22][N:23]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596520284-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

Product 1

HCID 144418476-[4-(3-Chloro-propoxy)-phenyl]-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 500 mL round bottom flask, 4-[4-(3-chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester (7.85 g, 26.3 mmol), and hydrazine monohydrate (2.55 mL, 52.7 mmol), in isopropanol (200 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 5.2 g (74%). MS m/z 267 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customPurification with silica gel chromatography
  5. washeluting with methylene chloride/methanol (95:5)
  6. customproduced 5.2 g (74%)

Sources & evidence

ORD record
ord-4d21869709f84f5ca6b81d13ec2c28ea
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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