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25514-67-4

5-CYANOGRAMINE synthesis

3synthesis methods
-

Yield:25514-67-4 94%

Reaction Conditions:

with glacial acetic acid in 1,4-dioxane at 20;

Steps:

25

Acetic acid (50 mL), formaldehyde (4.06 mL), and dimethylamine (9.01 mL) were added to a solution of 5-Cyanoindole (7. H g, 50.00 mmol) in 101.52 mL dioxane. The solution was stirred at room temperature overnight. The solution was evaporated in vacuo to give the crude active gramine. The crude active gramine was dissolved in water and adjusted pH to 11.0 with 5N NaOH. The product initially separated as oil but it solidified as a fine powder which was later collected by filtration, to give 9.67g (48.53 mmol, 94%) of product. TLC (silica Rf= 0.63, IPA/NH3/H20, 10:2:1 v/v/v). 1H NMR (DMSO) δ: 2.14 (s, 6H, 2CH3), 3.55 (s, 2H, CH2), 7.41 (m, 2H, Ar)5 7.53 (d, IH, Ar), 8.09 (s, IH, Ar), 11.50 (s, IH, NH).

References:

WO2007/75931,2007,A2 Location in patent:Page/Page column 41-42

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