Sodium Hydroxide → N-Hydroxybenzo[d][1,3]dioxole-5-carboximidamide

HRID 538607

Reaction equation

HRID 538607 reaction equation
O1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[NH2:13][OH:14].[OH-:15].[Na+]>CCO>[OH:14][NH:13][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:15][CH2:2][O:3][C:4]=2[CH:9]=1)=[NH:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 78136Benzo-1,3-dioxole-5-carbonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513224N-Hydroxybenzo[d][1,3]dioxole-5-carboximidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Benzo[1,3]dioxole-5-carbonitrile (5.0 g, 33.9 mmol) in EtOH (100 mL) was added hydroxylamine hydrochloride (4.68 g, 67.90 mmol) and NaOH (2.71 g, 67.9 mmol). The resulting reaction mixture was refluxed for 12 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added EtOH and filtered. The filtrate was evaporated under reduced pressure and used as such for the next step (crude yield 4.8 g, 78.68%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 12 h
  3. customAfter the completion of the reaction (TLC monitoring)
  4. concentrationthe mixture was concentrated
  5. additionadded EtOH
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed4964eb1abe4136a714c129c4b0a833
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Linked notes

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