N-(4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-yl)acetamide → N-(4-(2-(4-Aminonaphthalen-1-yloxy)ethyl)pyridin-2-yl)acetamide

HRID 1774364Notes

Reaction equation

HRID 1774364 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=2)=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 67457565N-(4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-yl)acetamide

Product 1

HCID 68232597N-(4-(2-(4-Aminonaphthalen-1-yloxy)ethyl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of N-(4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-yl)acetamide (570 mg, 1.62 mmol) in a mixture of AcOH: MeOH (6:1 v/v, 54 mL) was subjected to hydrogenation by passage through a Thales H-cube (1 mLmin−1, 30 mm, 10% Pt/C Cat-Cart, full H2, 45° C.). The solvent was removed by evaporation in vacuo, and, the residue was subjected to SCX capture and release to furnish the title compound, Intermediate B, (550 mg, 100%): m/z 322 (M+H)+ (ES+).

Workup

  1. customThe solvent was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-e4ac5201e4b540dc9eeb021b87138b24
Source dataset
uspto-grants-2016_02
Patent number
US09260410B2

Reaction notes

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