HCID 178498355, compound → HCID 13050867, compound

HRID 371298Notes

Reaction equation

HRID 371298 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[C:4](=[O:14])[C:3]=1[C:15]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[C:21]([Cl:28])[C:16]=1[C:17](OC)=[O:18]>[OH-].[Na+]>[Cl:28][C:21]1[C:16]2[C:17](=[O:18])[O:1][C:2]3[C:11](=[O:12])[C:10]4[C:9]([OH:13])=[CH:8][CH:7]=[CH:6][C:5]=4[C:4](=[O:14])[C:3]=3[C:15]=2[C:24]([O:25][CH3:26])=[CH:23][C:22]=1[CH3:27]

Participants

3

Reactant 1

HCID 178498355HCID 178498355, compound2×

Product 1

HCID 13050867HCID 13050867, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 20% aqueous sodium hydroxide was dissolved methyl 2-(3,5-dihydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methyl-6-chlorobenzoate as obtained in (1) and the solution was refluxed for 3 hours. The reaction mixture was allowed to cool, acidified, and extracted with ethyl acetate. The solvent layer was washed with water and dried. The solvent was then distilled off and the residue was dissolved in tetrahydrofuran (2 ml). After addition of acetic anhydride (2 ml), the crystals that separated out were recovered by filtration, washed with diethyl ether and dried to give crystals (70 mg) of 4-chloro-8-hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-5,7,12-trione.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe solvent layer was washed with water
  5. customdried
  6. distillationThe solvent was then distilled off
  7. dissolutionthe residue was dissolved in tetrahydrofuran (2 ml)
  8. additionAfter addition of acetic anhydride (2 ml)
  9. customthe crystals that separated out
  10. filtrationwere recovered by filtration
  11. washwashed with diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-f4c2d3ef57c44e3e86a51531db893f68
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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