Hydrazine hydrate (1:1) → HCID 21450250, compound

HRID 1579260Notes

Reaction equation

HRID 1579260 reaction equation
[OH:1][CH:2]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([CH2:11][CH2:12][C:13]([NH:15]C)=[O:14])=O)=[CH:7][CH:6]=1.O.[NH2:25]N>C(O)(=O)C>[OH:1][CH:2]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]2[CH2:11][CH2:12][C:13](=[O:14])[NH:15][N:25]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21450221HCID 21450221, compound

Product 1

HCID 21450250HCID 21450250, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[4-(2-Hydroxy-3-isopropylaminopropoxy)benzoyl]-N-methylpropionamide (5g, 0.015 mole) in 50% aqueous acetic acid (50 ml) was treated with hydrazine hydrate (2.4 ml, 0.047 mole) and heated under reflux for one hour. After evaporation under reduced pressure, the residue was dissolved in water, neutralised with aqueous sodium bicarbonate and extracted with dichloromethane. Evaporation of the dried organic solution gave 6-[4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (2.4 g, 50%, m.p. 108°-115°C). Crystallisation from water gave the pure pyridazinone, m.p. 116.5°-118°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. customAfter evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with dichloromethane
  6. customEvaporation of the dried organic solution

Sources & evidence

ORD record
ord-54e28cea72bd437a80fa75deb7843101
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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