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

HRID 26226
ノート
印刷プレビュー

反応式

HRID 26226 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26c83f0667db4e6fa80fd0c67fe6be88
出典データセット
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04148919

反応ノート

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