Acetic Anhydride → HCID 9888747, compound

HRID 1370320Notes

Reaction equation

HRID 1370320 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[CH:10]=[CH:9][C:8](=[O:14])[C:7]=2[N:6]=[CH:5][CH:4]=1.[F:15][C:16]([F:34])([F:33])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][CH:28]=[N:29]N(C)C)=[O:18].C(OC(=O)C)(=O)C>CC#N.C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[C:10]3[C:26]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:17](=[O:18])[C:16]([F:33])([F:15])[F:34])=[CH:27][CH:28]=[N:29][C:9]=3[C:8](=[O:14])[C:7]=2[N:6]=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 117899714-methoxyquinoline-5,8-dioneHCID 53710179HCID 53710179, compound

Product 1

HCID 9888747HCID 9888747, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

3.5 g (16 mmol) of 4-methoxyquinoline-5,8-dione, 7 g (24 mmol) of 4-(2-trifluoroacetamidophenyl)-1-dimethylamino-1-aza-1,3-butadiene and 15 mL of acetic anhydride in 200 mL of CH3CN are refluxed for 18 hours. After evaporating off the solvent on a rotary evaporator and purifying by filtration through silica (99.5/0.5 CH2Cl2/MeOH), 3 g of adduct are obtained. This compound is dissolved in 150 mL of toluene, 6 g of Pd/C (10%) are added and the reaction medium is refluxed overnight. 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 0.6 g of the compound in the form of a pale green powder.

Workup

  1. customAfter evaporating off the solvent
  2. customon a rotary evaporator
  3. filtrationpurifying by filtration through silica (99.5/0.5 CH2Cl2/MeOH), 3 g of adduct
  4. customare obtained
  5. temperaturethe reaction medium is refluxed overnight
  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-e1b4aabb6b194992a40b3d20beb63d43
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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