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

HRID 2067072Notes

Reaction equation

HRID 2067072 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][CH:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=2)[CH3:16])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.CC(O)=O.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=2)[CH3:16])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 584167824-(1-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 584167804-(1-(4-Aminonaphthalen-1-yloxy)ethyl)pyridin-2-amineYield 99%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4-(1-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-2-amine (23) (91 mg, 0.294 mmol) in MeOH (15 mL) and AcOH (3.0 mL) was passed through a Thales H-cube (1.0 mL·min−1, 30° C., 55 mm 10% Pt/C Cat-Cart, full hydrogen mode). The volatiles were removed under reduced pressure, leaving a purple solid, which was then subjected to SCX capture and release to give 4-(1-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-amine (24) (81 mg, 99%) as a purple oil: m/z 280 (M+H)+ (ES+).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customleaving a purple solid, which

Sources & evidence

ORD record
ord-dc336faec3b042b88229e49ad37c5aa2
Source dataset
uspto-grants-2012_10
Patent number
US08293748B2

Reaction notes

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