Water → HCID 22719974, compound

HRID 1582189Notes

Reaction equation

HRID 1582189 reaction equation
[OH-:1].[Na+].Cl.[Cl-].[CH3:5][O:6][CH2:7][CH2:8][N:9]1[C:13]2[C:14](=[O:23])[C:15]3[C:20]([C:21](=[O:22])[C:12]=2[N+:11]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[C:10]1[CH3:31])=[CH:19][CH:18]=[CH:17][CH:16]=3.O>C(O)C>[CH3:5][O:6][CH2:7][CH2:8][NH:9][C:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[C:12]=1[N:11]([CH2:24][C:25]1[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=1)[C:10](=[O:1])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22719982HCID 22719982, compound

Product 1

HCID 22719974HCID 22719974, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 M Sodium hydroxide aqueous solution (5.0 ml) was added to a solution of 1-(2-methoxyethyl)-2-methyl-3-(4-pyridylmethyl)-4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]imidazol-3-ium chloride monohydrochloride (1.1 g) in ethanol (30 ml) and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (fraction A: elution with ethyl acetate-hexane 1:1 solution, fraction B: elution with ethyl acetate). The fraction A was crystallized from diethyl ether to give N-[3-(2-methoxyethyl)amino-1,4-dihydro-1,4-dioxo-2-naphthalenyl]-N-(4-pyridylmethyl)acetamide (0.2 g) as a red powder. In this connection, the fraction B was crystallized from ethyl acetate to give a yellow powder (0.31 g) which was found to be the same compound, N-(2-methoxyethyl)-N-[3-(4-pyridylmethyl)amino-1,4-dihydro-1,4-dioxo-2-naphthalenyl]acetamide that will be described later in Example 37.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (fraction A:
  6. washelution with ethyl acetate-hexane 1:1 solution, fraction B
  7. washelution with ethyl acetate)
  8. customThe fraction A was crystallized from diethyl ether

Sources & evidence

ORD record
ord-52b7954499ff4b59bc46e725e96f060b
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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