1,4-Naphthoquinone → HCID 19701080, compound

HRID 861923Notes

Reaction equation

HRID 861923 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.CN(C)[N:15]=[CH:16][C:17]([F:20])=[CH:18][CH3:19]>C(Cl)(Cl)Cl>[F:20][C:17]1[CH:16]=[N:15][C:9]2[C:7](=[O:8])[C:5]3[C:4]([C:11](=[O:12])[C:10]=2[C:18]=1[CH3:19])=[CH:3][CH:2]=[CH:1][CH:6]=3

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 53662947HCID 53662947, compound

Product 1

HCID 19701080HCID 19701080, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of naphthoquinone (553 mg, 3.5 mmol) and 2-fluoro-2-butenal N,N-dimethylhydrazone was refluxed for 8 days in chloroform (15 ml.) After the solvent was evaporated at reduced pressure, the residue was chromatographed over silica gel column, eluting with petroleum ether-ethyl acetate (9:1) and yielded 63 mg (10%) of compound (I-k) and 90 mg (15%) of 3-fluoro-4-methyl-1-azaanthracen-9-10-dione. m.p. 190°-192° C. (CDCl3).

Workup

  1. customwas evaporated at reduced pressure
  2. customthe residue was chromatographed over silica gel column
  3. washeluting with petroleum ether-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-c3f49e9feb5947f590c5adec72fb63b1
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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