3-Hydroxypyridine → 3-(3-Nitrophenoxy)pyridine

HRID 1887436Notes

Reaction equation

HRID 1887436 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[OH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 212855723-(3-Nitrophenoxy)pyridineYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-fluoro-3-nitrobenzene (1 g, 7 mmol, 1 eq), 3-hydroxypyridine (674 mg, 7.09 mmol, 1.00 eq), K2CO3 (1.18 g, 8.54 mmol, 1.20 eq) and DMF (10 mL) were added to a microwave vial and microwaved at 200° C. for 30 minutes. The reaction was filtered and concentrated on silica gel (5 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 1.1 g (72%) of the title compound as a brown oil: 1H NMR (400 MHz, DMSO-d6) 8.49 (d, J=2.8 Hz, 1H), 8.46 (d, J=4.6 Hz, 1H), 8.02 (dd, J=8.2, 2.0 Hz, 1H), 7.78 (t, J=2.3 Hz, 1H), 7.70 (t, J=8.2 Hz, 1H), 7.60 (m, 1H), 7.54 (dd, J=8.3, 2.4 Hz, 1H), 7.49 (dd, J=8.4, 4.6 Hz, 1H); ES-MS [M+1]+: 217.2

Workup

  1. custommicrowaved at 200° C. for 30 minutes
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated on silica gel (5 g)
  4. washwashed with 50% ethyl acetate/hexane
  5. customThe solvents were removed in vacuo
  6. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e9ccb3613a79495a92865a9282f80201
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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