N-Hydroxyacetamidine → HCID 68567955, compound

HRID 747597Notes

Reaction equation

HRID 747597 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12]C(Cl)=O.[C:16](=[N:19][OH:20])([NH2:18])[CH3:17]>N1C=CC=CC=1>[CH3:17][C:16]1[N:18]=[C:12]([N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[O:20][N:19]=1

Participants

4

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-

Product 1

HCID 68567955HCID 68567955, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4.4 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride in 20 ml of pyridine are added 1.48 g of acetamidoxime, and the mixture is refluxed for 1 hour. The reaction medium is concentrated and taken up in ethyl acetate and water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 7/3 (v/v) toluene/ethyl acetate mixture to give 1.2 g of expected product.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. concentrationThe reaction medium is concentrated
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 7/3 (v/v) toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-dc301f6778224ebda82badc635b11c16
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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