Hydrazine hydrate (1:1) → 6-(4-Ethoxy-3-methoxyphenyl)-3[2H]pyridazinone

HRID 247390Notes

Reaction equation

HRID 247390 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH:12](N2CCOCC2)[C:13](O)=[O:14])=[CH:6][C:5]=1[O:23][CH3:24])[CH3:2].O.[NH2:26][NH2:27]>C(O)CCC>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](=[O:14])[NH:26][N:27]=2)=[CH:6][C:5]=1[O:23][CH3:24])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 201606434-(4-Ethoxy-3-methoxyphenyl)-2-morpholino-4-oxobutyric acid

Product 1

HCID 201606276-(4-Ethoxy-3-methoxyphenyl)-3[2H]pyridazinone

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4.5 g of 4-(4-ethoxy-3-methoxyphenyl)-2-morpholino-4-oxobutyric acid are boiled under reflux in 30 ml of 1-butanol with 6.7 g of 100% pure hydrazine hydrate for 8 hours. The reaction mixture is then evaporated in vacuo; the residue is boiled up in 100 ml of 2N hydrochloric acid, filtered off with suction and washed with water until free from acid. After drying, 2.1 g (65.6% of theory) of the title compound of m.p. 182°-184° are obtained; after recrystallization from ethanol/ethyl acetate, the product has a melting point of 186°.

Workup

  1. customThe reaction mixture is then evaporated in vacuo
  2. filtrationfiltered off with suction
  3. washwashed with water until free from acid
  4. customAfter drying

Sources & evidence

ORD record
ord-c8d297052164425da47c102271328e66
Source dataset
uspto-grants-1987_11
Patent number
US04707481

Reaction notes

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