(4-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitrophenyl)formamide → (2-Amino-4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}phenyl)formamide

HRID 547629Notes

Reaction equation

HRID 547629 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH:20]=[O:21])=[C:15]([N+:22]([O-])=O)[CH:14]=2)=[C:8]([O:25][CH3:26])[CH:7]=1>C(OCC)(=O)C.[Pd]>[NH2:22][C:15]1[CH:14]=[C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH:2]3[O:1][CH2:5][CH2:4][O:3]3)=[CH:7][C:8]=2[O:25][CH3:26])[CH:18]=[CH:17][C:16]=1[NH:19][CH:20]=[O:21]

Participants

4

Reactant 1

HCID 57585943(4-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitrophenyl)formamide

Product 1

HCID 57585922(2-Amino-4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}phenyl)formamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4-{[4-(1,3-Dioxolan-2-yl)-2-(methyloxy)phenyl]oxy}-2-nitrophenyl)formamide (430 mg) was hydrogenated in approximately 75 mL of ethyl acetate under an atmosphere of hydrogen over 100 mg of 10% Pd on carbon (wet, degussa type) for 3 days. The catalyst was filtered away and the filtrate was concentrated to give (2-amino-4-{[4-(1,3-dioxolan-2-yl)-2-(methyloxy) phenyl]oxy}phenyl)formamide, which was used without further purification. (M+1) 330.9, 1.79 min (LC/MS method B)

Workup

  1. filtrationThe catalyst was filtered away
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cbfc8e2a0cab4caf8b7270c672accb44
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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