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

HRID 46718

반응식

HRID 46718 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2b0a682cfd634875950be7402ba2dab1
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04174856

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