HCID 15068883, compound → HCID 15068894, compound

HRID 2106732Notes

Reaction equation

HRID 2106732 reaction equation
[C:1]1([O:11][C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][C:17]=2[N+:18]([O-])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(O)C>[C:1]1([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[NH2:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 15068883HCID 15068883, compound

Product 1

HCID 15068894HCID 15068894, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-(1-naphthyloxy)-4-nitropyridine-N-oxide (7.5 g) in 250 ml ethanol containing 0.5 g PtO2 was hydrogenated at 50 psi for five hours and filtered through Celite. The filtrate was concentrated to 6 g oil. This oil was purified by HPLC (silica, 50% ethyl acetate in dichloromethane) to give 4 g oil. Final purification was achieved by converting the oil to the hydrochloride salt in methanol/ether and immediately thereafter reconverting the salt to the free base with sodium carbonate to afford 3.5 g solid product. This solid was recrystallized from diethyl ether to give a solid, 2.3 g, m.p. 107°-109°.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated to 6 g oil
  3. customThis oil was purified by HPLC (silica, 50% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-4ea1d9e90cb44661898fcf40c71e409b
Source dataset
uspto-grants-1990_06
Patent number
US04931457

Reaction notes

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