5-(2,6-Dichloro-4-nitro-phenoxy)-2-hydroxy-N-nonyl-benzamide → 5-(4-Amino-2,6-dichloro-phenoxy)-2-hydroxy-N-nonyl-benzamide

HRID 584014Notes

Reaction equation

HRID 584014 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[C:24]([Cl:31])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:23])=[C:9]([CH:22]=1)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:11]>CCO.CCOC(C)=O.[Pd]>[NH2:28][C:26]1[CH:25]=[C:24]([Cl:31])[C:3]([O:4][C:5]2[CH:6]=[CH:7][C:8]([OH:23])=[C:9]([CH:22]=2)[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:11])=[C:2]([Cl:1])[CH:27]=1

Participants

5

Reactant 1

HCID 223449585-(2,6-Dichloro-4-nitro-phenoxy)-2-hydroxy-N-nonyl-benzamide

Product 1

HCID 223449235-(4-Amino-2,6-dichloro-phenoxy)-2-hydroxy-N-nonyl-benzamideYield 72.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-hydroxy-N-nonyl-benzamide (168 mg, 0.36 mmol) in a mixture of EtOH (3 ml) and EtOAc (3 ml) was added catalyst (10% Pd/C, 100 mg). The resulting mixture was hydrogenated at 55 psi for 1.5 h at RT. The mixture was filtered through Celite® and concentrated to give the title compound of Step E (115 mg) as a tan solid. The title product of Step E was used without further purification in the next step. MS (APCl+) Calc.: 438.1. Found: 439.3 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b2d94db08538440b8297679dd74b19a3
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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