HCID 15284565, compound → HCID 19701073, compound

HRID 861922Notes

Reaction equation

HRID 861922 reaction equation
CN(C)[N:3]=[CH:4][C:5](=[CH2:7])[CH3:6].[C:9]1([C:15]2[C:16](=[O:29])[NH:17][C:18]3[C:23]([CH:24]=2)=[C:22]([O:25]C)[CH:21]=[CH:20][C:19]=3[O:27]C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[CH3:6][C:5]1[CH:7]=[C:21]2[C:20](=[N:3][CH:4]=1)[C:19](=[O:27])[C:18]1[NH:17][C:16](=[O:29])[C:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:24][C:23]=1[C:22]2=[O:25]

Participants

4

Reactant 2

HCID 15284565HCID 15284565, compoundHCID 542371221,1-Dimethyl-2-(2-methylprop-2-en-1-ylidene)hydrazine

Product 1

HCID 19701073HCID 19701073, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methacrolein dimethylhydrazone (90 mg, 0.75 mmol) in one portion was added to a solution of 3-phenyl-5,8-dimethoxy-2-(1H)-quinolinone (190 mg, 0.71 mmol) in chloroform (50 ml.) The solution was agitated at room temperature for 3 hours and was evaporated. The residue was chromatographed over silica gel, eluting with ethyl acetate to give 120 mg (50%) of 6-methyl-3-phenyl-1H-1,8-diazaanthracen-2,9,10-trione (I-j). m.p. 275° C.

Workup

  1. customwas evaporated
  2. customThe residue was chromatographed over silica gel
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a49a1312e45e4bd88ca68ad2eb82c618
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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