Hydrazine hydrate (1:1) → HCID 90411100, compound

HRID 626554Notes

Reaction equation

HRID 626554 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:20])[CH3:21])[CH:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90410934HCID 90410934, compound

Product 1

HCID 90411100HCID 90411100, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (1.08 g, 3.57 mmol) in MeOH (30 mL) was treated with hydrazine hydrate (1.00 g, 19.98 mmol) followed by Raney Nickel (0.300 g, 5.11 mmol) and stirred at RT for 3 h. The solids were removed via filtration through diatomaceous earth, washed with DCM and MeOH and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (900 mg, 93%) as an off-white solid. MS (ESI) m/z: 273.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-218defcb5bb94bca8819c52e70d71890
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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