Toluene → 5,6,7,8-Tetrahydro-2-anilinoacridone

HRID 128096

反応式

HRID 128096 の反応式
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:16](F)(F)[C:17]([OH:19])=O.[C:22]1(C)[CH:27]=[CH:26]C=[CH:24][CH:23]=1>O>[C:1]1([NH:7][C:8]2[CH:13]=[C:12]3[C:11]([NH:14][C:24]4[CH2:23][CH2:22][CH2:27][CH2:26][C:16]=4[C:17]3=[O:19])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7564N-Phenyl-p-phenylenediamine

生成物 1

HCID 140291045,6,7,8-Tetrahydro-2-anilinoacridone収率 89%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 73.6 g (0.4 mol) of N-phenyl-p-phenylenediamine, 72 g (0.4 mol) of a mixture of the methyl and ethyl esters of 2-cyclohexanonecarboxylate (Aldrich Chemical Co., 40% methyl, 60% ethyl ester) 0.8 ml of trifluoroacetic acid and 1200 ml of toluene was refluxed for 1 hour in a flask equipped with a Dean-Stark water separator. The solvent was removed under vacuum and the resultant oil was dissolved in 500 ml of Dowtherm® A. This solution was added over 1 hour to 100 ml of refluxing Dowtherm® A in a flask equipped with mechanical stirrer, nitrogen flow and a steam heated condenser. Reflux was continued for 1 hour after the addition was complete. The mixture was cooled to room temperature and the precipitated product was filtered. The product was washed with four 200 ml aliquots of methanol. Vacuum oven drying at 80° C. overnight gave 99.9 g (89% yield) of 1,2,3,4-tetrahydro-7-(phenyl)amino-9(10H)acridinone. The product was identified by microanalysis.

後処理

  1. temperaturewas refluxed for 1 hour in a flask
  2. customThe solvent was removed under vacuum
  3. dissolutionthe resultant oil was dissolved in 500 ml of Dowtherm® A
  4. additionThis solution was added over 1 hour to 100 ml of refluxing Dowtherm® A in a flask
  5. customequipped with mechanical stirrer
  6. temperaturenitrogen flow and a steam heated condenser
  7. temperatureReflux
  8. additionafter the addition
  9. filtrationthe precipitated product was filtered
  10. washThe product was washed with four 200 ml aliquots of methanol
  11. customVacuum oven drying at 80° C. overnight

出典と根拠

ORDレコード
ord-6bb441d6f47f409f89b9977fb0052494
出典データセット
uspto-grants-1981_03
特許番号
US04258190

関連ノート

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