Ethyl Acetate → Chinoin 170

HRID 1285162Notes

Reaction equation

HRID 1285162 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15](=[N:17][OH:18])[NH2:16])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C[O-].[Na+].[C:22](OCC)(=O)[CH3:23]>CO>[CH3:22][C:23]1[O:18][N:17]=[C:15]([CH2:14][N:10]2[C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=3[N:8]=[CH:9]2)[N:16]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 30574902-(Theophyllin-7-yl)-acetamidoximeHCID 10942334Sodium Methoxide

Product 1

HCID 139570Chinoin 170Yield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.04 g. of 2-(theophyllin-7-yl)-acetamidoxime, 2.16 g. of sodium methylate and 10 cm3 ethyl acetate are heated under shaking and under pressure in 150 cm3 methanol at 100° C. for 8.5 hours. After processing 4.8 g. (87% yield) of 7-[(5-methyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline are obtained. M.p.: 135°-136° C.

Sources & evidence

ORD record
ord-9880b85227844ad3b713d627f97bb011
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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