Acetic Anhydride → HCID 9908770、化合物

HRID 1370319ノート

反応式

HRID 1370319 の反応式
[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]

参加物

7

反応物 3

HCID 7918Acetic AnhydrideHCID 3883065,8-Dihydroquinoline-5,8-dioneHCID 53710179HCID 53710179、化合物

生成物 1

HCID 9908770HCID 9908770、化合物収率 5%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d36924d01ebf4bd9b6a70cecb53c945f
出典データセット
uspto-grants-2003_06
特許番号
US06583150B1

反応ノート

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