N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide → N-[3-(3,4-Diamino-phenoxy)-phenyl]-acetamide

HRID 491635Notes

Reaction equation

HRID 491635 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[O:7][C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[NH2:21])[O:7][C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 86002098N-[3-(3,4-dinitro-phenoxy)-phenyl]-acetamide

Product 1

HCID 17755037N-[3-(3,4-Diamino-phenoxy)-phenyl]-acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[3-(3,4-Dinitro-phenoxy)-phenyl]-acetamide (Step A, 0.4 g, 1.3 mmol, 1.0 eq.) was dissolved in MeOH (10 mL) and the atmosphere was replaced by argon. A catalytic amount of 10% Pd/C was added and the argon was replaced by a H2 atmosphere. The mixture was stirred for 16 h at RT at balloon pressure. The Pd/C was filtered and the obtained N-[3-(3,4-diamino-phenoxy)-phenyl]-acetamide was used crude in the next step. MS m/z=259.1 (M+H)+Calc'd for C14H15N3O2: 257.29.

Workup

  1. filtrationThe Pd/C was filtered

Sources & evidence

ORD record
ord-1b719e8ceb0b466b9089cfbe6da9a24b
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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