2-Nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenol → 2-amino-5-[3-(3-pyridinyl)-1,2,4-oxadiazol-5-yl]Phenol

HRID 713799Notes

Reaction equation

HRID 713799 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:11]=2)=[CH:6][C:5]=1[OH:21])([O-])=O>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:11]=2)=[CH:6][C:5]=1[OH:21]

Participants

4

Reactant 1

HCID 670260952-Nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenol

Product 1

HCID 549242552-amino-5-[3-(3-pyridinyl)-1,2,4-oxadiazol-5-yl]Phenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 25 (284 mg, 1 mmol) in tetrahydrofuran (10 mL) was stirred with Raney®-nickel (Aldrich, 100 mg) under hydrogen at ambient temperature for 2 hours. The catalyst was then removed by filtration and the organic solution concentrated to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 5.67 (s, 2H), 6.74 (d, J=8.1 Hz, 1H), 7.41-7.50 (m, 2H), 7.62 (dd, J=8.3, 4.6 Hz, 1H), 8.39 (dt, J=8.2, 1.9, 1.7 Hz, 1H), 8.78 (dd, J=4.7, 1.7 Hz, 1H), 9.20 (d, J=1.7 Hz, 1H), 9.74 (s (broad), 1H) ppm; MS (DCl/NH3) m/z 255 (M+H)+.

Workup

  1. customThe catalyst was then removed by filtration
  2. concentrationthe organic solution concentrated

Sources & evidence

ORD record
ord-f8fa7ea1528d4752830b113f2e77ced9
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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