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

HRID 718143Notes

Reaction equation

HRID 718143 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[N:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=1>CCOC(C)=O.[Pd]>[NH2:8][C:6]1[N:5]=[CH:4][C:3]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 90409722N-(4-((4-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

Product 1

HCID 90410511N-(4-((6-amino-4-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamideYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-((4-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (0.36 g, 1.249 mmol) in EtOAc (15 mL) was treated with 10% Pd/C (50% w/w water, 0.133 g, 0.125 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was concentrated to dryness to afford N-(4-((6-amino-4-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (320 mg, 99%). 1H NMR (400 MHz, DMSO-d6): δ 10.47 (s, 1H), 8.11 (d, J=5.7 Hz, 1H), 7.66 (s, 1H), 7.55 (d, J=2.4 Hz, 1H), 6.55 (dd, J=5.7, 2.4 Hz, 1H), 6.37 (s, 1H), 5.88 (s, 2H), 2.02 (s, 3H), 1.93 (s, 3H); MS (ESI) m/z: 259.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with EtOAc
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c42f6d630115468b81894ee147d3a254
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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