Water → N-[(2H-1,3-Benzodioxol-5-yl)methylidene]hydroxylamine

HRID 2120909Notes

Reaction equation

HRID 2120909 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.Cl.[NH2:13][OH:14].O>CO>[OH:14][N:13]=[CH:7][C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 8438PiperonalHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 95280N-[(2H-1,3-Benzodioxol-5-yl)methylidene]hydroxylamineYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperonal(15.0 g, 0.10 mol) was dissolved in methanol(150 ml), and hydroxylamine hydrochloride(10.5 g, 0.15 mol) and water(15 ml) were added thereto. The mixture was stirred for 1 hour at room temperature, then excess water was added, and the resulting mixture was stirred for further 1 hour. The white solid thus obtained was washed with water under reduced pressure, filtered, and dried to give (hydroxyimino)-(benzo[3,4-d]1,3-dioxolan-5-yl)methane(15.7 g, Yield 95%).

Workup

  1. stirringthe resulting mixture was stirred for further 1 hour
  2. customThe white solid thus obtained
  3. washwas washed with water under reduced pressure
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-2666f8d7a8b043ecb6dac185c35c8ff3
Source dataset
uspto-grants-2004_02
Patent number
US06693126B2

Reaction notes

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