Hydroxylamine → HCID 3347217, compound

HRID 1403175Notes

Reaction equation

HRID 1403175 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][OH:11]>C(O)C>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 966574-Iodobenzaldehyde

Product 1

HCID 3347217HCID 3347217, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 4-iodobenzaldehyde (2000 mg, 8.620 mmol) in ethanol (9.000 mL) cooled in an ice bath, hydroxylamine (569.4 μL of 50% w/v, 8.620 mmol) was added and the reaction was removed from ice bath and stirred at rt for 1 h. After this time the reaction mixture was heated at 50° C. for 1 h and then cooled to rt and concentrated in vacuo to leave the title compound as a white solid (2.03 g, 95% yield); 1H NMR (400 MHz, DMSO) d 7.38 (m, 2H), 7.76 (m, 2H), 8.11 (s, 1H) and 11.37 (s, 1H) ppm; MS (ES+) 248.1.

Workup

  1. temperaturecooled in an ice bath
  2. customthe reaction was removed from ice bath
  3. temperatureAfter this time the reaction mixture was heated at 50° C. for 1 h
  4. temperaturecooled to rt
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e0f6c41e10a416988142668775341bc
Source dataset
uspto-grants-2014_12
Patent number
US08912198B2

Reaction notes

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