Hydroxylamine → HCID 86738972, compound

HRID 1154048Notes

Reaction equation

HRID 1154048 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]2[C:14](=[O:29])[C:15]([CH3:28])([CH2:18][C:19](OC3C=CC=CC=3)=[O:20])[C:16](=[O:17])[N:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:30][OH:31].Cl.NO.[OH-].[K+]>COCCOC.CO>[OH:31][NH:30][C:19]([CH2:18][C:15]1([CH3:28])[C:14](=[O:29])[N:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]2[C:16]1=[O:17])=[O:20]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20435956HCID 20435956, compound

Product 1

HCID 86738972HCID 86738972, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

2.2 g of phenyl 5-tert.butoxycarbonyl-hexahydro-2-methyl-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-2-acetate in 12 ml of 1,2-dimethoxyethane were treated with 9 ml of methanolic hydroxylamine (prepared by dissolving 1.38 g of hydroxylamine hydrochloride in methanol, adding 1.12 g of potassium hydroxide pellets in methanol to a total volume of 14 ml and filtering the solution before use). After 18 hours, the solvent was removed, 300 ml of ethyl acetate were added and the mixture was washed with dilute sodium chloride solution followed by saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and evaporated, there being thus obtained an oil which crystallized from ethyl acetate to give 0.98 g of tert.butyl hexahydro-2-[(N-hydroxycarbamoyl)methyl]-2-methyl-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate having a melting point of 157°-165° C. (decomposition).

Workup

  1. customprepared
  2. filtrationfiltering the solution before use)
  3. customthe solvent was removed
  4. addition300 ml of ethyl acetate were added
  5. washthe mixture was washed with dilute sodium chloride solution
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated
  8. customthere being thus obtained an oil which
  9. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1fd4c19b3ef44409935d498efb8a0238
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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