Acetic Anhydride → HCID 9908770, compound

HRID 1370319Notes

Reaction equation

HRID 1370319 reaction equation
[N:1]1[C:10]2[C:9](=[O:11])C=C[C:6](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:13][C:14]([F:32])([F:31])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=[CH:25][CH:26]=[N:27]N(C)C)=[O:16].[C:33](OC(=O)C)(=O)[CH3:34]>CC#N.C1(C)C=CC=CC=1.[Pd]>[F:32][C:14]([F:13])([F:31])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[C:25]2[C:6](=[O:12])[C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:10]=3[C:9](=[O:11])[C:26]=2[N:27]=[CH:34][CH:33]=1)=[O:16]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 3883065,8-Dihydroquinoline-5,8-dioneHCID 53710179HCID 53710179, compound

Product 1

HCID 9908770HCID 9908770, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

1 g (6.3 mmol) of quinoline-5,8-dione, 3.59 g (12.6 mmol) of 4-(2-trifluoroacetamidophenyl)-1-dimethylamino-1-aza-1,3-butadiene and 7.5 mL of acetic anhydride in 175 mL of CH3CN are refluxed for 24 hours. After evaporating off the solvent on a rotary evaporator and purifying by filtration on silica (95/5 CH2Cl2/MeOH), the adduct is obtained. This compound is dissolved in 150 mL of toluene, 6.2 g of Pd/C (10%) are added and the reaction medium is refluxed for 12 hours. After filtering off and washing the residue with MeOH and then with CHCl3, the filtrate is concentrated on a rotary evaporator and then purified by flash chromatography on a column of silica (95/5 CH2Cl2/MeOH) to give 0.125 g of compound CRL 8277 in the form of a yellow powder.

Workup

  1. customAfter evaporating off the solvent
  2. customon a rotary evaporator
  3. filtrationpurifying by filtration on silica (95/5 CH2Cl2/MeOH)
  4. customthe adduct is obtained
  5. temperaturethe reaction medium is refluxed for 12 hours
  6. filtrationAfter filtering off
  7. washwashing the residue with MeOH
  8. concentrationwith CHCl3, the filtrate is concentrated on a rotary evaporator
  9. custompurified by flash chromatography on a column of silica (95/5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-d36924d01ebf4bd9b6a70cecb53c945f
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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