HCID 10921303, compound → HCID 10881677, compound

HRID 1451699Notes

Reaction equation

HRID 1451699 reaction equation
[CH3:1][N:2]([CH3:13])[N:3]=[CH:4]/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:14][C:15]1[C:24]2[C:23](=[O:25])[CH:22]=[CH:21][C:20](=[O:26])[C:19]=2[NH:18][C:17](=[O:27])[CH:16]=1>C(Cl)(Cl)Cl>[CH3:14][C:15]1[C:24]2[C:23](=[O:25])[C:22]3[CH:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH:5]=[CH:4][NH:3][C:21]=3[C:20](=[O:26])[C:19]=2[NH:18][C:17](=[O:27])[CH:16]=1.[CH3:1][N:2]([CH3:13])[C:22]1[C:23](=[O:25])[C:24]2[C:15]([CH3:14])=[CH:16][C:17](=[O:27])[NH:18][C:19]=2[C:20](=[O:26])[CH:21]=1

Participants

5

Reactant 2

HCID 10921303HCID 10921303, compoundHCID 70196513HCID 70196513, compound

Product 2

HCID 10857314HCID 10857314, compoundHCID 10881677HCID 10881677, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 233 mg (1.34 mmol) of trans-cinnamaldehyde N,N-dimethylhydrazone was added to a solution of 4-methyl-1H-quinoline-2,5,8-trione (127 mg, 0.67 mmol) in dry chloroform (120 ml). The reaction was stirred under nitrogen at room temperature for 3 days, with periodical additions of solvent (100 ml each 12 h). A further amount of 166 mg (0.61 mmol) of the hydrazone was added, and the reaction was refluxed for 24 h and evaporated to dryness, and the residue was purified by silica gel chromatography using a gradient elution, starting with neat dichloromethane to dichloromethane/ethyl acetate (7:3), to yield 204 mg of the starting diene, 72 mg (35%) of 2 and 160 mg of 6-dimethylamino-4-methyl-1H-quinoline-2,5,8-trione.

Workup

  1. temperaturethe reaction was refluxed for 24 h
  2. customevaporated to dryness
  3. customthe residue was purified by silica gel chromatography
  4. washa gradient elution

Sources & evidence

ORD record
ord-101f15311b1749ce9f0fe96699a16d53
Source dataset
uspto-grants-1997_02
Patent number
US05605905

Reaction notes

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