N-(2,3-dihydroxypropionyl)-3-amino-5-nitroaniline → HCID 178467278, compound

HRID 261364Notes

Reaction equation

HRID 261364 reaction equation
[OH:1][CH:2]([CH2:16][OH:17])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([NH2:15])[CH:7]=1)=[O:4].[C:18]([C:21]1[C:22](=[O:32])[O:23][C:24]([OH:31])=[C:25]([C:28](=O)[CH3:29])[C:26]=1[OH:27])(=[O:20])[CH3:19]>CO>[C:18]([C:21]1[C:22](=[O:32])[O:23][C:24](=[O:31])[C:25](=[C:28]([NH:15][C:8]2[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:6]([NH:5][C:3](=[O:4])[CH:2]([CH2:16][OH:17])[OH:1])[CH:7]=2)[CH3:29])[C:26]=1[OH:27])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 20394926N-(2,3-dihydroxypropionyl)-3-amino-5-nitroanilineHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178467278HCID 178467278, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 785 mg (3.3 mmole) of N-(2,3-dihydroxypropionyl)-3-amino-5-nitroaniline and 690 mg (3.3 mmole) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one in 30 ml of methanol was heated under reflux for 30 minutes. After cooling, the crystalline product was filtered and dried in vacuum to give 616 mg of 5-acetyl-4-hydroxy-3-[1-(3-glyceroylamino-5-nitrophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe crystalline product was filtered
  5. customdried in vacuum

Sources & evidence

ORD record
ord-ae0c70339a8842b996e0a8016d577a60
Source dataset
uspto-grants-1979_08
Patent number
US04165365

Reaction notes

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