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

HRID 2085648ノート

反応式

HRID 2085648 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1ae7912960ca49cdb69d93c7cb3779bc
出典データセット
uspto-grants-2004_04
特許番号
US06720452B2

反応ノート

読み込み中…