Ammonia → 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole

HRID 46718

反応式

HRID 46718 の反応式
[CH3:1][N:2]([CH3:17])[C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.O[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2.N>P(Cl)(Cl)(Cl)=O>[C:9]1([C:7]2([C:6]3[CH:15]=[CH:16][C:3]([N:2]([CH3:17])[CH3:1])=[CH:4][CH:5]=3)[C:33]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][C:25]=3[C:20]3[C:21](=[CH:22][CH:23]=[CH:24][CH:19]=3)[O:8]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 222AmmoniaHCID 107374-(Dimethylamino)benzophenoneHCID 7000092-(1H-indol-2-yl)phenol

生成物 1

HCID 126326896-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole収率 80.2%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

11.26 g of 4-dimethylaminobenzophenone and 10.5 g of 2-(2'-hydroxyphenyl)-indole are stirred in 50 ml of phosphorus oxychloride for 4 hours under reflux. The reaction mixture is poured onto ice and rendered alkaline with ammonia and the resulting precipitate is then filtered off. Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid and precipitating with ammonia and water gives a slightly impure product, which is purified through a column, packed with 80 g of silica gel/ethyl acetate. Crystallisation from ethyl acetate/ethanol gives 16.7 g of 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole of the formula ##STR17## in the form of yellowish crystals with a melting point of 229°-231° C. On silton clay, this colour-forming agent develops a blue colour with a λ max of 600 nm.

後処理

  1. temperatureunder reflux
  2. additionThe reaction mixture is poured onto ice
  3. filtrationthe resulting precipitate is then filtered off
  4. dissolutionRepeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid
  5. customprecipitating with ammonia and water
  6. customgives a slightly impure product, which
  7. customis purified through a column
  8. customCrystallisation from ethyl acetate/ethanol

出典と根拠

ORDレコード
ord-2b0a682cfd634875950be7402ba2dab1
出典データセット
uspto-grants-1979_11
特許番号
US04174856

関連ノート

読み込み中…