Sodium Hydroxide → HCID 20309483, compound

HRID 596694Notes

Reaction equation

HRID 596694 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:19][CH2:20][CH:21]([OH:28])[CH2:22][NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14](OC)=[O:15])=O)(=[O:3])[CH3:2].O.[NH2:30][NH2:31].[OH-].[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:19][CH2:20][CH:21]([OH:28])[CH2:22][NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[C:9]([C:10]2[CH2:12][CH2:13][C:14](=[O:15])[NH:30][N:31]=2)[CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20309603HCID 20309603, compound

Product 1

HCID 20309483HCID 20309483, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 3-[5-acetamido-2-(3-t-butylamino-2-hydroxypropoxy)benzoyl]propionate (0.21g) and hydrazine hydrate (0.12 ml) in glacial acetic acid (5 ml) was heated under reflux of 16 hours. Evaporation of the reaction mixture under reduced pressure gave a glassy residue to which was added sodium hydroxide solution (2N, 10 ml). The resulting solution was extracted well with chloroform, the combined organic phases washed with water, dried and evaporated to give a white brittle residue which was recrystallised from isopropanol/ether to give 6-[5-acetamido-2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone as a white solid (0.16g, 80% m.p. 102°-109° C; M+, 376, M 376).

Workup

  1. temperatureunder reflux of 16 hours
  2. customEvaporation of the reaction mixture under reduced pressure
  3. customgave a glassy residue to which
  4. extractionThe resulting solution was extracted well with chloroform
  5. washthe combined organic phases washed with water
  6. customdried
  7. customevaporated
  8. customto give a white brittle residue which
  9. customwas recrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-f006e3eb607e498aadd97e3fe38b0f2e
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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