Hydroxylamine → HCID 136377090, compound

HRID 1409577Notes

Reaction equation

HRID 1409577 reaction equation
Cl.NO.[OH-:4].[K+].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]#[N:21].[NH2:22]O.[C:24]([C:30]([O:32]C)=O)#[C:25][C:26]([O:28][CH3:29])=[O:27]>CO>[CH3:29][O:28][C:26]([C:25]1[N:21]=[C:20]([CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH3:6])[NH:22][C:30](=[O:32])[C:24]=1[OH:4])=[O:27]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86710276HCID 86710276, compound

Product 1

HCID 136377090HCID 136377090, compoundYield 0.12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of hydroxylamine hydrochloride (979 mg, 14.1 mmol) in methanol (15 ml) and a solution of potassium hydroxide (790 mg, 14.1 mmol) in methanol (15 ml) were combined at 0° C. Solid (KCl) was removed by filtration. The filtrate was added to 2-(2′-methylbiphenyl-2-yl)acetonitrile (1.46 g, 7.04 mmol) and heated at 60° C. overnight. An extra equivalent of NH2OH in MeOH solution was added and heating was continued for 5 h. The mixture was cooled and then concentrated in vacuo. The residue was taken up into CHCl3 (30 ml) and to this was added dimethyl acetylenedicarboxylate (1.00 g, 7.04 mmol). The mixture was heated at 60° C. overnight, cooled and evaporated. The residue was transferred to a microwave vial and xylene (8 ml) was added. The vial was capped and heated in the microwave oven at 140° C. for 3 h, cooled. Chromatography (silica gel; 10% to 100% EtOAc in hexanes) provided the desired product as an off-white solid (0.003 g; 0.12%). LCMS: m/z=351 (MH+).

Workup

  1. customwere combined at 0° C
  2. customSolid (KCl) was removed by filtration
  3. temperatureheating
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated in vacuo
  6. temperatureThe mixture was heated at 60° C. overnight
  7. temperaturecooled
  8. customevaporated
  9. additionwas added
  10. customThe vial was capped
  11. temperatureheated in the microwave oven at 140° C. for 3 h
  12. temperaturecooled

Sources & evidence

ORD record
ord-a03d3455fddd495ea99a43fee5417a98
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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