3-Hydroxypyridine → HCID 19042898, compound

HRID 1371960Notes

Reaction equation

HRID 1371960 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.F[C:9]1[CH:10]=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([CH3:15])[CH:14]=1>CN(C=O)C.[Cl-].[Na+].O>[CH3:15][C:13]1[CH:14]=[C:9]([CH:10]=[CH:11][C:12]=1[N+:16]([O-:18])=[O:17])[O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 79713-HydroxypyridineHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 19042898HCID 19042898, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Rinse 35% oil dispersion of KH (12 g, 11 mmol) with 100 mL hexanes twice and dry under vacuum before cooling in an ice bath. Add 100 mL dry DMF then a solution of 3-hydroxypyridine (10 g, 105 mmol) in 100 mL DMF dropwise. Treat with a solution of 5-fluoro-2-nitrotoluene (16.3 g, 105 mmol) in 50 mL DMF to obtain a dark solution. Stir at ambient temperature for 1 hour, pour the mixture into 1 liter of brine and extract twice with 200 mL of EtOAc. Combine the extracts and wash twice with 500 mL brine, dry over MgSO4 and concentrate to 24 g of a dark oil. Purification by chromatography 20% EtOAc in hexanes give the title compound as an oil: ISMS 231 (M+1); C12H10N2O3: calcd: C, 62.61; H, 4.38; N, 12.17; found: C, 62.63; H, 4.58; N, 12.06.

Workup

  1. washRinse 35% oil dispersion of KH (12 g, 11 mmol) with 100 mL hexanes twice
  2. customdry under vacuum
  3. temperaturebefore cooling in an ice bath
  4. additionAdd 100 mL dry DMF
  5. customto obtain a dark solution
  6. extractionextract twice with 200 mL of EtOAc
  7. washwash twice with 500 mL brine
  8. dry with materialdry over MgSO4
  9. concentrationconcentrate to 24 g of a dark oil
  10. customPurification by chromatography 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-4ba3a1a6ecdb42739f5286f6fb7bd5ee
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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