Ammonium Hydroxide → HCID 67325553, compound

HRID 871855Notes

Reaction equation

HRID 871855 reaction equation
[NH4+].[OH-].[CH3:3][CH:4]1[CH2:6][C:5]1([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[C:7]([NH2:9])=[O:8]>O1CCCC1.[Zn]>[CH3:3][CH:4]1[CH2:6][C:5]1([C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 67325480HCID 67325480, compound

Product 1

HCID 67325553HCID 67325553, compoundYield 289.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.56 g (54.49 mmol) of zinc powder in 15 mL of concentrated aqueous 33% NH4OH solution are added 1.2 g (5.45 mmol) of the product prepared in step 9.1 dissolved in 15 mL of tetrahydrofuran. The mixture is stirred for 1 hour at room temperature, the zinc is then separated out by filtration and the mixture is extracted with ether. The organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. The oily residue is purified by chromatography on a column of silica, eluting with a cyclohexane/ethyl acetate gradient (70/30 to 60/40). 3 g of the expected product are obtained in the form of a yellow oil. Quantitative yield.

Workup

  1. customthe zinc is then separated out by filtration
  2. extractionthe mixture is extracted with ether
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe oily residue is purified by chromatography on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient (70/30 to 60/40)

Sources & evidence

ORD record
ord-6eded6adab5c43ccb5e7b29d20671839
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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