2-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine → 2-Amino-4-((4-aminonaphthalen-1-yloxy)methyl)pyridine

HRID 2067001Notes

Reaction equation

HRID 2067001 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([N+:20]([O-])=O)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1>CO.C(O)(=O)C.[Pt]>[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 584167602-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine

Product 1

HCID 584167572-Amino-4-((4-aminonaphthalen-1-yloxy)methyl)pyridineYield 94.5%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-Amino-4-[(4-nitronaphthalen-1-yloxy)methyl]pyridine (3) (4.50 g, 15.24 mmol) in methanol (200 mL) and glacial acetic acid (200 mL) was passed through a Thales ‘H-cube’ flow reactor (2 mL min−1, 40° C., 55 mm 10% Pt/C Cat-Cart®, full H2) and the volatiles were then removed in vacuo. The crude product was subjected to SCX capture and release eluting with 1% ammonia in MeOH solution and the solvent was removed in vacuo to give 2-amino-4-[(4-aminonaphthalen-1-yloxy)methyl]pyridine (4) (3.82 g, 94%) as a mauve solid: m/z 266 (M+H)+ (ES+).

Workup

  1. customthe volatiles were then removed in vacuo
  2. washeluting with 1% ammonia in MeOH solution
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b8e955af110d44fbaf563376462d89d6
Source dataset
uspto-grants-2012_10
Patent number
US08293771B2

Reaction notes

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