Sodium Carbonate → HCID 20309480, compound

HRID 972771Notes

Reaction equation

HRID 972771 reaction equation
O.[NH2:2][NH2:3].[C:4]([NH:8][CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:14]=1[C:15]([CH2:17][CH2:18][C:19](OCC)=[O:20])=O)([CH3:7])([CH3:6])[CH3:5].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O>[C:4]([NH:8][CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:14]=1[C:15]1[CH2:17][CH2:18][C:19](=[O:20])[NH:2][N:3]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 20309488HCID 20309488, compound

Product 1

HCID 20309480HCID 20309480, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Hydrazine hydrate (1.57 ml, 0.0314 mole) was added to a stirred solution of ethyl 3-[2-(3-t-butylamino-2-hydroxypropoxy)-4-chlorobenzoyl]propionate (2.4 g, 0.0065 mole) in glacial acetic acid (36 ml) and the solution was heated under reflux for 90 minutes. Evaporation under reduced pressure gave an oil which was dissolved in water, treated with an excess of aqueous sodium carbonate solution and the mixture was extracted with dichloromethane. Evaporation of the dried organic extracts gave an oil which ws purified on a silica column by elution with mixtures of chloroform and methanol to give 6-[2-(3-t-butylamino-2-hydroxypropoxy)-4-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone (1.1 g, 50%, m.p. 195°). The hemisulphate, crystallised from ethanol, had m.p. 250° (decomposition).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 90 minutes
  3. customEvaporation under reduced pressure
  4. customgave an oil which
  5. extractionthe mixture was extracted with dichloromethane
  6. customEvaporation of the dried organic extracts
  7. customgave an oil which
  8. customws purified on a silica column by elution with mixtures of chloroform and methanol

Sources & evidence

ORD record
ord-b90461c749654e47b03724c532ea6bcd
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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