HCID 10921303, compound → HCID 10880089, compound

HRID 1451700Notes

Reaction equation

HRID 1451700 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=[O:12])[CH:9]=[CH:8][C:7](=[O:13])[C:6]=2[NH:5][C:4](=[O:14])[CH:3]=1.CN(C)[N:17]=[CH:18][C:19]([CH2:21][CH3:22])=[CH2:20]>C(Cl)(Cl)Cl>[CH2:21]([C:19]1[CH:20]=[C:9]2[C:8](=[N:17][CH:18]=1)[C:7](=[O:13])[C:6]1[NH:5][C:4](=[O:14])[CH:3]=[C:2]([CH3:1])[C:11]=1[C:10]2=[O:12])[CH3:22]

Participants

4

Reactant 2

HCID 10921303HCID 10921303, compoundHCID 53941239HCID 53941239, compound

Product 1

HCID 10880089HCID 10880089, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 150 mg (0.9 mmol) of 4-methyl-1H-quinoline-2,5,8-trione and 150 mg (0.79 mmol) of 2-ethylacrolein dimethylhydrazone in dry chloroform (130 ml) was stirred at room temperature for five minutes. After evaporation of the solvent, the residue was purified by silica gel chromatography using ethyl acetate as eluent to yield 29 mg of the starting hydrazone, 64 mg (30%) of 5 and 60 mg of 6-dimethylamino-4-methyl-1H-quinoline-2,5,8-trone.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-37b1f207081641c793c00e2a40c5e5e1
Source dataset
uspto-grants-1997_02
Patent number
US05605905

Reaction notes

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