Pyridine → HCID 14180578, compound

HRID 1904963Notes

Reaction equation

HRID 1904963 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]1[O:13][CH2:14][CH2:15][O:16][C:6]=1[C:5]2=[O:17].[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1.[O:31]1CC[CH2:33][CH2:32]1>CN(C)C1C=CN=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][C:18](=[O:20])[CH3:19])=[C:7]1[O:13][CH2:14][CH2:15][O:16][C:6]1=[C:5]2[O:17][C:32](=[O:31])[CH3:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran2×HCID 14180572HCID 14180572, compound

Product 1

HCID 14180578HCID 14180578, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalyst

Procedure

A supension of 6-chloro-2,3-ethylenedioxy-1,4-naphthoquinone (2 g) in tetrahydrofuran was hydrogenated at 1 atm over 10% palladium-on-carbon (0.5 g). When the solution was colorless, a solution of acetic anhydride (4 g), pyridine (3.16 g) and 4-dimethylaminopyridine (0.2 g) in tetrahydrofuran (25 mL) was added. After 1 hour, the solution was filtered and evaporated, and the resdiue was dissolved in dichloromethane. The organic layer was washed with 1 M hydrcholoric acid and brine and then dried. The dried layer was filtered and evaported. Crystallization from ether gave 1.20 g of 6-chloro-2,3-ethylenedioxy-1,4-diacetyloxynaphthlene, mp 179°-180° C.

Workup

  1. filtrationthe solution was filtered
  2. customevaporated
  3. dissolutionthe resdiue was dissolved in dichloromethane
  4. washThe organic layer was washed with 1 M hydrcholoric acid and brine
  5. customdried
  6. filtrationThe dried layer was filtered
  7. customCrystallization from ether

Sources & evidence

ORD record
ord-c1e901aa685e422d8692bb5385e91f22
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

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