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Sulfuric Acid → 7-amino-6,7-dihydro [5H] benzocycloheptene

HRID 26226
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HRID 26226 반응식
S(=O)(=O)(O)O.O[CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][CH:9]([NH2:18])[CH2:8]1.O1CCOCC1>O>[NH2:18][CH:9]1[CH:8]=[CH:7][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 545180195xi-hydroxy-7-amino-6,7,8,9-tetrahydro [5 H] benzocycloheptene

생성물 1

HCID 213252467-amino-6,7-dihydro [5H] benzocycloheptene수율 59.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
20 °C

실험 절차

12 ml of 18N sulfuric acid were added to a refluxing mixture of 5.6 g of the product of Step C and 60 ml of dioxane and the mixture was refluxed for 2 hours and then was cooled to 20° C. The mixture was poured into 300 ml of water and the neutral fraction was extracted with ether. The aqueous phase was made alkaline with sodium hydroxide addition and was extracted with ethyl acetate. The ethyl acetate extracts were washed with aqueous sodium chloride solution, dried, filtered and evaporated to dryness to obtain 5 g of raw product. The latter was chromatographed over silica gel and was eluted with an 8-2-1 ethyl acetate-benzene-triethylamine mixture to obtain 3 g of 7-amino-6,7-dihydro [5H] benzocycloheptene in the form of a brown oil.

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionthe neutral fraction was extracted with ether
  3. additionwith sodium hydroxide addition
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate extracts were washed with aqueous sodium chloride solution
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto obtain 5 g of raw product
  10. customThe latter was chromatographed over silica gel
  11. washwas eluted with an 8-2-1 ethyl acetate-benzene-triethylamine mixture

출처 및 근거

ORD 기록
ord-26c83f0667db4e6fa80fd0c67fe6be88
출처 데이터셋
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04148919

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