Ammonium Chloride → 5-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085648노트

반응식

HRID 2085648 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:22][C:19]1[CH:20]=[CH:21][C:2]([Cl:1])=[C:3]([CH:18]=1)[C:4]([NH:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2)=[O:5]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 584852N-(1-Adamantylmethyl)-2-chloro-5-nitrobenzamide

생성물 1

HCID 227314875-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide수율 87.5%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

A solution of 2-chloro-5-nitro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 29a, 0.50 g) and ammonium chloride (0.5 g) were dissolved in 50% aqueous ethanol. Iron powder (0.5 g) was added and the mixture stirred at reflux temperature for 3 h before being cooled and the solids removed by filtration. The mother liquors were treated with 10% sodium hydroxide solution and the product extracted into ethyl acetate. The organic solution was washed with brine, dried over sodium sulphate (Na2SO4) and concentrated to give a residue which was purified by silica gel chromatography to give the sub-title compound as a white solid (0.4 g).

후처리

  1. temperatureat reflux temperature for 3 h
  2. temperaturebefore being cooled
  3. customthe solids removed by filtration
  4. additionThe mother liquors were treated with 10% sodium hydroxide solution
  5. extractionthe product extracted into ethyl acetate
  6. washThe organic solution was washed with brine
  7. dry with materialdried over sodium sulphate (Na2SO4)
  8. concentrationconcentrated
  9. customto give a residue which
  10. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-1ae7912960ca49cdb69d93c7cb3779bc
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720452B2

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