Hydrochloric Acid → Aminostilbene

HRID 2084442노트

반응식

HRID 2084442 반응식
[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Sn]>>[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 199081-Nitro-2-(2-phenylethenyl)benzeneHCID 5352426Tin atom

생성물 1

HCID 139378Aminostilbene수율 76.4%

실험 절차

At room temperature, a mixture of 12.9 g (0.057 mol) of l-phenyl-2-(2-nitro-phenyl)-ethene and 210 ml of 17% strength aqueous hydrochloric acid is admixed with 38.7 g of tin powder and slowly heated to reflux temperature. The mixture is boiled under reflux for 2 hours and then cooled to room temperature and extracted repeatedly with diethyl ether. The organic phase is concentrated under reduced pressure. The residue that remains is admixed with water, and the resulting mixture is neutralized by addition of dilute aqueous sodium hydroxide solution and then extracted repeatedly with methylene chloride. The combined organic phases are dried over sodium sulphate and subsequently concentrated under reduced pressure. The residue that remains is chromatographed over silica gel using cyclohexane:ethyl acetate=3:1. Concentration of the eluate gives 8.5 g (76.4% of theory) of 2-(2-phenylethen-1-yl)-aniline in the form of a solid substance of melting point 80° C.

후처리

  1. temperatureslowly heated
  2. temperatureto reflux temperature
  3. temperatureunder reflux for 2 hours
  4. extractionextracted repeatedly with diethyl ether
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. additionthe resulting mixture is neutralized by addition of dilute aqueous sodium hydroxide solution
  7. extractionextracted repeatedly with methylene chloride
  8. dry with materialThe combined organic phases are dried over sodium sulphate
  9. concentrationsubsequently concentrated under reduced pressure
  10. customThe residue that remains is chromatographed over silica gel

출처 및 근거

ORD 기록
ord-054c80aaaeb744a9b29e666188facd4d
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716881B2

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