HCID 15068884, compound → HCID 15068895, compound

HRID 2106733Notes

Reaction equation

HRID 2106733 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:15]=[N+:16]([O-])[CH:17]=[CH:18][C:19]=2[N+:20]([O-])=O)=[CH:5][CH:4]=1>C(O)C.O=[Pt]=O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[NH2:20])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 15068884HCID 15068884, compound

Product 1

HCID 15068895HCID 15068895, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of PtO2 (0.3 g) in 5 ml of ethanol was added 3-(4-methoxy-1-naphthyloxy)-4-nitropyridine-N-oxide (7.2 g) in 245 ml of ethanol. The material was hydrogenated under pressure (50 PSI) by shaking the slurry on a Parr apparatus for six hours. The mixture was filtered and the filtrate concentrated to yield an oil (5.2 g). This oil was eluted with 5% methanol/DCM on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil which solidified on standing (4.36 g). This material was triturated with ether to yield a solid, 2.85 g, m.p. 126°-129° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bbf0f299f9844435b1717213ef6e56a1
Source dataset
uspto-grants-1990_06
Patent number
US04931457

Reaction notes

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