HCID 178498355, compound → HCID 13050867, compound

HRID 1648949Notes

Reaction equation

HRID 1648949 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 ahydride (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 ahydride (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-d980de5769af4e56b1dc7a4af3caa21a
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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