Dichloromethane → 4-(2-(4-Aminonaphthalen-1-yloxy)ethyl)pyridin-3-amine

HRID 872404Notes

Reaction equation

HRID 872404 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]=[CH:19][C:18]=2[NH2:23])=[CH:6][CH:5]=1)([O-])=O.CCOC(C)=O.C(Cl)Cl.[H][H]>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]=[CH:19][C:18]=2[NH2:23])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 584167784-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 584167794-(2-(4-Aminonaphthalen-1-yloxy)ethyl)pyridin-3-amineYield 96.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine (17) (700 mg, 2.263 mmol) in a mixture of MeOH (50 mL), EtOAc (25 mL), and DCM (25 mL) was passed through a Thales H-cube (10% Pt/C 30 mm, 1.0 mL·min−1, at 40° C., full hydrogen mode). The solvent was removed in vacuo to give 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-3-amine (18) as a brown solid (612 mg, 92%). m/z 280 (M+H)+ (ES+).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ba8f03b9245041cda8826fd7b2087c05
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Reaction notes

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