Pyridine → HCID 12285286, compound

HRID 414626Notes

Reaction equation

HRID 414626 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:16])[C:5]2[C:10]([C:11](=[O:15])[C:12]=1[O:13][CH3:14])=[CH:9][CH:8]=[CH:7][CH:6]=2.[H][H].[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=CC=1.[O:32]1CC[CH2:34][CH2:33]1>[Pd]>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([O:16][C:19](=[O:21])[CH3:20])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]=1[O:15][C:33](=[O:32])[CH3:34]

Participants

7

Reactant 5

HCID 1049PyridineHCID 31362,3-Dimethoxy-1,4-naphthoquinoneHCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran2×HCID 178418361HCID 178418361, compound

Product 1

HCID 12285286HCID 12285286, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2,3-dimethoxy-1,4-naphthoquinone (20.0 g) in tetrahydrofuran (150 mL) was hydrogenated at atmospheric pressure over Pd-C (10%, 0.5 g) until the solution was colorless, approximately 4 hours. While still under a blanket of hydrogen, a solution of acetic anhydride (20 mL) and pyridine (18 mL) in tetrahydrofuran (50 mL) was added to the mixture. After stirring for 1 hour, the mixture was evaporated. The residue was dissolved in ether (100 mL) and was washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated. Recrystallization from ether afforded 2,3-dimethoxy-1,4-diacetyloxynaphthalene (22.5 g), m.p. 138°-139° C.

Workup

  1. customthe mixture was evaporated
  2. dissolutionThe residue was dissolved in ether (100 mL)
  3. washwas washed with 1M hydrochloric acid (3×50 mL) and with brine (2×50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-19b26f0fa3e14605b27837b7515269b8
Source dataset
uspto-grants-1988_12
Patent number
US04792556

Reaction notes

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