Isoniazid → HCID 178465645, compound

HRID 973981Notes

Reaction equation

HRID 973981 reaction equation
[C:1]([C:4]1[C:5]([OH:15])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=O)[CH3:2].[C:16]([NH:24][NH2:25])(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>CCOCCO>[C:16]([NH:24][N:25]=[C:1]([C:4]1[C:5]([OH:15])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2])(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 178467321HCID 178467321, compound

Product 1

HCID 178465645HCID 178465645, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

20.3 g of 3-acetyl-2,4-dihydroxyquinoline and 13.8 g of isonicotinic acid hydrazide are condensed in 180 ml of ethyl cellosolve analogously to Example 1, yielding 27.2 g of 3-acetyl-2,4-dihydroxyquinoline isonicotinoylhydrazone. 3.2 g of this product are suspended in 25 ml of dimethylformamide and treated with a solution of 2.4 g of zinc(II) acetate·2H2O in 35 ml of dimethylformamide. The resulting mixture is stirred for 2 hours at 90°-100° C. and the product is then isolated by filtration and subsequently washed with isopropanol and then with water. After the product has been dried under vacuum at 70°-80° C., 3.2 g of a yellow powder of the following formula: ##STR86## as the 1:1 zinc complex are obtained.

Sources & evidence

ORD record
ord-9303ba6e0b754bf39526fc80285b23d6
Source dataset
uspto-grants-1991_11
Patent number
US05066695

Reaction notes

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