Hydroxylamine → 4-((1,3-Dioxolan-2-yl)methyl)-N'-hydroxybenzimidamide

HRID 332696Notes

Reaction equation

HRID 332696 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.[NH2:15][OH:16]>C(O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([C:11](=[N:15][OH:16])[NH2:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 38007934-((1,3-Dioxolan-2-yl)methyl)benzonitrile

Product 1

HCID 866769114-((1,3-Dioxolan-2-yl)methyl)-N'-hydroxybenzimidamideYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-((1,3-dioxolan-2-yl)methyl)benzonitrile (1.40 g, 7.41 mmol) in ethanol (10 mL), was added 50% aqueous hydroxylamine (5 mL), and the resultant mixture was heated at 80° C. for 16 hours. The solvent was evaporated at reduced pressure, and the residue partitioned between ethyl acetate and brine. The organic phase was removed, and the aqueous phase was extracted with further ethyl acetate (×2). The combined organic extracts were dried with aqueous magnesium sulfate and evaporated at reduced pressure to afford the title compound (1.21 g, 73%).

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was extracted with further ethyl acetate (×2)
  5. dry with materialThe combined organic extracts were dried with aqueous magnesium sulfate
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-9414414e55cd49c29ed4f6c7d8985207
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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