Acetic Anhydride → HCID 178515264, compound

HRID 1370325Notes

Reaction equation

HRID 1370325 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[CH:13][CH:14]=[N:15]N(C)C)=[O:4].C(OC(=O)C)(=O)C.[O:28]=[C:29]1[CH:38]=[CH:37][C:36](=[O:39])[C:35]2[NH:34][C:33](=[O:40])[CH:32]=[CH:31][C:30]1=2>C(#N)C.[Pd]>[OH:40][C:33]1[CH:32]=[CH:31][C:30]2[C:29](=[O:28])[C:38]3[C:12]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[NH:5][C:3](=[O:4])[C:2]([F:1])([F:19])[F:20])=[CH:13][CH:14]=[N:15][C:37]=3[C:36](=[O:39])[C:35]=2[N:34]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 2675922,5,8(1H)-QuinolinetrioneHCID 53710179HCID 53710179, compound

Product 1

HCID 178515264HCID 178515264, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

1.9 g (6.5 mmol) of 4-(2-trifluoroacetamidophenyl)-1-dimethylamino-1-aza-1,3-butadiene, 2.2 mL of acetic anhydride and 1.6 g of Pd/C (10%) are successively added to a solution of 5,8-dioxocarbostyril (1.04 g, 5.9 mmol) in 500 mL of acetonitrile. The reaction medium is refluxed for 15 hours under nitrogen. After evaporating off the solvent on a rotary evaporator, the crude product obtained is purified by flash chromatography on silica (CH2Cl2 and then 95/5 CH2Cl2/MeOH) to give 400 mg of a yellow powder of compound CRL 8249 (or of its oxo tautomer in position 8).

Workup

  1. temperatureThe reaction medium is refluxed for 15 hours under nitrogen
  2. customAfter evaporating off the solvent
  3. customon a rotary evaporator
  4. customthe crude product obtained
  5. customis purified by flash chromatography on silica (CH2Cl2

Sources & evidence

ORD record
ord-bfd0d2f6a6734ddd9bca94843f4767e4
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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