Water → HCID 22719957, compound

HRID 1582183Notes

Reaction equation

HRID 1582183 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.C(N(C(C)C)CC)(C)C.[Cl:18][C:19]1[C:20](=[O:31])[C:21]2[C:26]([C:27](=[O:30])[C:28]=1Cl)=[CH:25][CH:24]=[CH:23][CH:22]=2.O>C1C=CC=CC=1>[Cl:18][C:19]1[C:20](=[O:31])[C:21]2[C:26]([C:27](=[O:30])[C:28]=1[NH:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8342DichloneHCID 81531DiisopropylethylamineHCID 266781(Pyrazin-2-yl)methanamine

Product 1

HCID 22719957HCID 22719957, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(Aminomethyl)pyrazine (3.2 g) and diisopropylethylamine (5.8 ml) were added to a solution of 2,3-dichloro-1,4-dihydro-1,4-dioxonaphthalene (3.0 g) in benzene (90 ml) and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution and the resulting precipitate was removed by filtration and then the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with chloroform) to give 2-chloro-1,4-dihydro-1,4-dioxo-3-[(2-pyrazinylmethyl)amino]naphthalene (0.23 g) as a light brown powder.

Workup

  1. customthe resulting precipitate was removed by filtration
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (elution with chloroform)

Sources & evidence

ORD record
ord-eb4bbc92faa041ad96ccd1522b79eea3
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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