(5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone → (5-Allyloxy-2-amino-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 641848Notes

Reaction equation

HRID 641848 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:22]([O-])=O)=[C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[O:12])[CH:10]=1)[CH:2]=[CH2:3]>C(O)(=O)C.[Fe]>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:22])=[C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:17][CH:18]=2)=[O:12])[CH:10]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 59259161(5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 45139629(5-Allyloxy-2-amino-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

To an ice chilled solution of 16 g (5-allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone in 65 ml acetic acid are added 21.8 g iron powder. A precipitate that is formed is brought into solution by addition of additional acetic acid. After stirring for 16 h at r.t. the reaction mixture is filtered and basified by addition of aqueous potassium hydroxide solution. Extraction with dichloromethane yields (5-allyloxy-2-amino-phenyl)-(4-isopropyl-phenyl)-methanone.

Workup

  1. customA precipitate that is formed
  2. filtrationis filtered
  3. additionbasified by addition of aqueous potassium hydroxide solution
  4. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-63a3b6d101f24aa6a77399fd8177432d
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

Loading…