1,4-Naphthoquinone → HCID 19701072, compound

HRID 861924Notes

Reaction equation

HRID 861924 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:19])=[CH2:18]>C(Cl)(Cl)Cl>[F:19][C:17]1[CH2:18][C:10]2[C:11](=[O:12])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[C:9]=2[NH:15][CH:16]=1

Participants

4

Reactant 2

HCID 85301,4-Naphthoquinone2×HCID 54457150HCID 54457150, compound

Product 1

HCID 19701072HCID 19701072, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of naphthoquinone (632 mg, 4 mmol) and 2-fluoro-2-propenal N,N-dimethylhydrazone was refluxed for 22 hours in dry chloroform (15 ml.) Another portion of naphthoquinone (0.41 g, 2.59 mmol) was added and the reflux continued for 3 more hours. After the solvent was evaporated at reduced pressure, silica gel column chromatography with elution with ethyl-ether-petroleum ether (1:1) yielded 187 mg (21%) of compound (I-1) and 42 mg (5%) of 3-fluoro-1,4-dihydro-1-azaanthracen-9,10-dione. m.p. 214° C. (MeOH).

Workup

  1. additionwas added
  2. customAfter the solvent was evaporated at reduced pressure, silica gel column chromatography with elution with ethyl-ether-petroleum ether (1:1)

Sources & evidence

ORD record
ord-0ab587a2166f4f38b173e1eeed055e7e
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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