Hydrazine hydrate (1:1) → HCID 20309483, compound

HRID 1763322Notes

Reaction equation

HRID 1763322 reaction equation
O.[NH2:2][NH2:3].[C:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:22][CH2:23][CH:24]([OH:31])[CH2:25][NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:12]([CH:21]=1)[C:13]([CH2:15][CH2:16][C:17](OC)=[O:18])=O)(=[O:6])[CH3:5]>C(O)(=O)C>[C:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:22][CH2:23][CH:24]([OH:31])[CH2:25][NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:12]([C:13]2[CH2:15][CH2:16][C:17](=[O:18])[NH:2][N:3]=2)[CH:21]=1)(=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20309603HCID 20309603, compound

Product 1

HCID 20309483HCID 20309483, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrazine hydrate (0.0785 ml, 0.00157 mole) was added to a stirred solution of methyl 3-[5-acetamido-2-(3-t-butylamino-2-hydroxypropoxy)benzoyl]propionate (0.21 g, 0.0005 mole) in glacial acetic acid (2 ml) and the solution was heated under reflux for 90 minutes. The residue after evaporation was treated with an excess of sodium bicarbonate solution and the solution evaporated to dryness under reduced pressure. The residue was extracted with dichloromethane and the dried extract evaporated to dryness. An aqueous solution of the residue was washed with two small portions of dichloromethane and then evaporated to an oily residue, which with ethyl acetate gave 6-[5-acetamido-2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (0.16 g, 80%, m.p. 165°-168°).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 90 minutes
  3. customThe residue after evaporation
  4. additionwas treated with an excess of sodium bicarbonate solution
  5. customthe solution evaporated to dryness under reduced pressure
  6. extractionThe residue was extracted with dichloromethane
  7. extractionthe dried extract
  8. customevaporated to dryness
  9. washAn aqueous solution of the residue was washed with two small portions of dichloromethane
  10. customevaporated to an oily residue, which with ethyl acetate

Sources & evidence

ORD record
ord-affb74e08b22412787ddf5a09c8874d4
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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