3,5-Dinitroaniline → HCID 178467279, compound

HRID 1704707Notes

Reaction equation

HRID 1704707 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].[C:14]([C:17]1[C:18](=[O:28])[O:19][C:20]([OH:27])=[C:21]([C:24](=O)[CH3:25])[C:22]=1[OH:23])(=[O:16])[CH3:15]>CO>[C:14]([C:17]1[C:18](=[O:28])[O:19][C:20](=[O:27])[C:21](=[C:24]([NH:7][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=2)[CH3:25])[C:22]=1[OH:23])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 120683,5-DinitroanilineHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178467279HCID 178467279, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedures of Example 4, an equimolar mixture of 3,5-dinitroaniline and 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one in methanol was reacted to give 5-acetyl-4-hydroxy-3-[1-(3,5-dinitrophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione. A solution of the latter (3.0 g., 0.008 mol) in 30 ml. of dimethylformamide was hydrogenated over 200 mg. of 10% palladium-on-carbon at 50 psi. When absorption stopped the catalyst was filtered and the filtrate poured into 200 ml. of ice-water. The resulting product was filtered, washed with water and dried to give 5-acetyl-4-hydroxy-3-[1-(3,5-diaminophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. above 350° C. (dec.).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-5bd6b95fab594f5ba4fb12da0fe0d35f
Source dataset
uspto-grants-1978_11
Patent number
US04127646

Reaction notes

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