Acetamidrazone HCl → HCID 136102517, compound

HRID 2402647Notes

Reaction equation

HRID 2402647 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:13](=O)[C:14]([O:16]CC)=O.[CH3:20]/[C:21](/[NH2:24])=[N:22]/[NH2:23].Cl>CCO>[CH3:20][C:21]1[NH:24][C:14](=[O:16])[C:13]([CH2:12][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])=[N:23][N:22]=1

Participants

4

Reactant 2

HCID 12239607Acetamidrazone HClHCID 57680977Ethyl 3-(1,3-dioxoisoindolin-2-yl)-2-oxopropanoate

Product 1

HCID 136102517HCID 136102517, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxopropanoate [J. Org. Chem., (1985), 50 (1), 91](4.29 g, 16.4 mmol), acetamidrazone hydrochloride (1.80 g, 16.4 mmol) in anhydrous EtOH (85.8 mL) was heated to 80° C. for 3 h then cooled to rt and stirred for an additional 16 h. The reaction mixture was filtered through a fritted funnel resulting in 3.28 g, (73% yield) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (s, 3H), 4.73 (s, 2H) and 7.74-8.12 (m, 4H); MS (ES+): m/z 271.08 [MH+].

Workup

  1. filtrationThe reaction mixture was filtered through a fritted funnel

Sources & evidence

ORD record
ord-adef4d71c2134743963438abaa28ccb5
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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