2-Amino-3-chloro-1,4-naphthoquinone → HCID 15345814, compound

HRID 1385201Notes

Reaction equation

HRID 1385201 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>S(=O)(=O)(O)O>[O:14]=[C:3]1[C:2]2[N:1]=[C:18]([C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[CH3:15])[O:19][C:11]=2[C:10](=[O:13])[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

4

Reactant 2

HCID 177482-Amino-3-chloro-1,4-naphthoquinoneHCID 702762-Methylbenzoyl chloride

Product 1

HCID 15345814HCID 15345814, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 5.00 g (24 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 37 mL (280 mmol) of 2-methylbenzoic acid chloride, 8 drops of concentrated sulfuric acid are added with protection from light. After 7 h of reflux and complete cooling, the ocher precipitate that forms is filtered through fritted glass, washed with ether, and purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50). The yellow powder obtained after evaporation of the solvent is uncolored, and recrystallized in dichloromethane to produce 2.34 g of 4,9-dihydro-4,9-dioxo-2-(2-methylphenyl)-naphtho[2,3-d]oxazole in the form of yellow crystals.

Workup

  1. temperatureAfter 7 h of reflux
  2. filtrationcomplete cooling, the ocher precipitate that forms is filtered through fritted glass
  3. washwashed with ether
  4. custompurified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 50/50)
  5. customThe yellow powder obtained
  6. customafter evaporation of the solvent
  7. customrecrystallized in dichloromethane

Sources & evidence

ORD record
ord-7faa9c06d2594d6d89ac8138943c90fe
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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