Sodium Hydroxide → 3-(Pyridin-3-yloxy)aniline

HRID 1887437Notes

Reaction equation

HRID 1887437 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)([O-])=O.[OH-].[Na+]>Cl.CO.[Zn]>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:5]=[C:4]([CH:16]=[CH:15][CH:14]=2)[NH2:1])[CH:9]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 212855723-(3-Nitrophenoxy)pyridine

Product 1

HCID 212855823-(Pyridin-3-yloxy)anilineYield 85%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Compound 4 (1.613 g, 7.461 mmol, 1.000 eq) was dissolved in 1N HCl in MeOH (75 mL) and zinc (1.46 g, 22.3 mmol, 3.00 eq) was added. The reaction was stirred for 1 hour and additional zinc (975 mg, 14.9 mmol, 2 eq) was added to drive the reaction to completion as determined by TLC. The reaction was neutralized with 1N NaOH (75 mL), filtered and extracted (3×) with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 555 mg (85%) of the title compound as a brown oil: 1H NMR (400 MHz, DMSO-d6) δ 8.33-8.31 (m, 2H), 7.39-7.38 (m, 2H), 7.01 (t, J=8.0 Hz, 1H), 6.35 (dd, J=8.0, 1.6 Hz, 1H), 6.19 (t, J=2.2 Hz, 1H), 6.14 (dd, J=7.9, 2.0 Hz, 1H), 5.27 (s, 2H); ES-MS [M+1]+: 187.2.

Workup

  1. customthe reaction to completion
  2. filtrationfiltered
  3. extractionextracted (3×) with CH2Cl2
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-384af55dbfac470eac6658e98830e586
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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