Acetic Anhydride → Chinoin 170

HRID 1285160Notes

Reaction equation

HRID 1285160 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:19](OC(=O)C)(=O)[CH3:20]>C(O)(=O)C>[CH3:19][C:20]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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 30574902-(Theophyllin-7-yl)-acetamidoxime

Product 1

HCID 139570Chinoin 170Yield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15.12 g of 2-(theophyllin-7-yl)-acetamidoxime are heated on water bath for two hours with a mixture of 120 cm3 acetic acid and 8 cm3 of acetic anhydride. The solvent is distilled off and 16.06 g. (91%) of 7-[(5-methyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline are obtained. M.p.: 135° C. (methanol).

Workup

  1. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-62e428e27c3148ecb744d87231d5de80
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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