N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide → N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 2278928Notes

Reaction equation

HRID 2278928 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:19]([O-])=O)[N:3]=1>CO.[Pd]>[NH2:19][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 90410470N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

Product 1

HCID 90426152N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (0.44 g, 1.526 mmol) in MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.162 g, 0.153 mmol) and hydrogenated (1 atm) at RT for 24 h. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate concentrated to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (370 mg, 94%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.46 (s, 1 H), 8.10 (d, J=5.7 Hz, 1 H), 7.53 (d, J=2.3 Hz, 1 H), 7.13 (d, J=8.7 Hz, 1 H), 6.53 (dd, J=5.7, 2.4 Hz, 1 H), 6.32 (d, J=8.7 Hz, 1 H), 5.91 (s, 2 H), 2.02 (s, 3 H), 2.01 (s, 3 H); MS (ESI) m/z: 259.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d63040840bed43c692c49d42aea199fa
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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