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

HRID 2085648Notes

Reaction equation

HRID 2085648 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1ae7912960ca49cdb69d93c7cb3779bc
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

Loading…