Acetic Acid → 6-(4-Benzyloxyphenoxy)pyridin-3-ylamine

HRID 1260541Notes

Reaction equation

HRID 1260541 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>CO.[Zn]>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[N:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27996982-(4-Benzyloxyphenoxy)-5-nitropyridine

Product 1

HCID 288183036-(4-Benzyloxyphenoxy)pyridin-3-ylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

2-(4-Benzyloxyphenoxy)-5-nitropyridine (7.84 g, 24.32 mmol) and zinc (15.16 g, 231.8 mmol) were suspended in 300 ml of methanol. Under argon 5.2 ml of acetic acid were slowly added dropwise at room temperature. After 1 h the mixture was filtered and the filtrate was concentrated. The crude product obtained was further reacted without purification.

Workup

  1. filtrationAfter 1 h the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-03a05b46932a4a53a9031ef9a7a68682
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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