Hydrochloric Acid → 1H-Indole-3-ethanamine, 7-chloro-

HRID 343450

反応式

HRID 343450 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.C(O[CH:14](OCC)[CH2:15][CH2:16][CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O)C.Cl>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:9][CH:14]=[C:15]2[CH2:16][CH2:17][NH2:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dione

生成物 1

HCID 1457091H-Indole-3-ethanamine, 7-chloro-

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A 10.0 g sample of 2-chlorophenylhydrazine hydrochloride and 17.9 g of 4-phthalimidobutyraldehyde diethyl acetal were stirred in 200 mL ethanol with 1 mL 5N HCl. The mixture was concentrated to a residue which was slurried in a small amount of methylene chloride. A yellow solid was collected and vacuum dried at 40° C. The solid was stirred in 500 mL ethanol. Hydrazine hydrate (14 g) was added and the mixture was heated at reflux for 14 hours. A 60 mL sample of 5N HCl was added and the mixture was heated at reflux for 1 hour. The mixture was allowed to cool and was concentrated to a residue. The residue was partitioned between 1N NaOH and chloroform. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined extracts were dried (Na2SO4) and concentrated to an oil. The oil was chromatographed on silica gel using a gradient of 0-10% methanol in chloroform containing 0.2% ammonium hydroxide. Fractions containing product were concentrated to an oil which was taken up in a small amount of methanol and added to ethereal HCl. A solid was collected, washed with diethyl ether, and vacuum dried at 50° C.

後処理

  1. concentrationThe mixture was concentrated to a residue which
  2. customA yellow solid was collected
  3. customvacuum dried at 40° C
  4. additionHydrazine hydrate (14 g) was added
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 14 hours
  7. additionA 60 mL sample of 5N HCl was added
  8. temperaturethe mixture was heated
  9. temperatureat reflux for 1 hour
  10. temperatureto cool
  11. concentrationwas concentrated to a residue
  12. customThe residue was partitioned between 1N NaOH and chloroform
  13. customThe organic layer was separated
  14. extractionthe aqueous layer was extracted with chloroform
  15. dry with materialThe combined extracts were dried (Na2SO4)
  16. concentrationconcentrated to an oil
  17. customThe oil was chromatographed on silica gel using a gradient of 0-10% methanol in chloroform containing 0.2% ammonium hydroxide
  18. additionFractions containing product
  19. concentrationwere concentrated to an oil which
  20. additionadded to ethereal HCl
  21. customA solid was collected
  22. washwashed with diethyl ether, and vacuum
  23. customdried at 50° C.

出典と根拠

ORDレコード
ord-cf428d227db942a2a2eeec72ac6fdd15
出典データセット
uspto-grants-1999_01
特許番号
US05861425

関連ノート

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