3-Pyridinecarboxaldehyde → HCID 86759539, compound

HRID 392442Notes

Reaction equation

HRID 392442 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.N[C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.C([BH3-])#[N:18].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[OH:16][C:12]1[CH:11]=[C:10]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][C:3]=2[CH2:7][NH2:18])[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 115683-AminophenolHCID 5003444Sodium cyanoborohydride

Product 1

HCID 86759539HCID 86759539, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

3-Pyridinecarboxaldehyde (0.550 g, 5 mmol) and 3-aminophenol (0.540 g, 5 mmol) were dissolved into methanol (15 ml). To the solution was added a mixture of sodium cyanoborohydride (0.378 g, 6 mmol) and zinc chloride (0.408 g, 3.0 mmol) in methanol at room temperature. The reaction mixture was stirred for 2.5 h. Most of the methanol was evaporated under reduced pressure. Ice water was added to the residue. It was filtered and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound. 1H NMR: 8.53 (s,1H), 8.45 (d,1H,J=3.9 Hz), 7.72 (d,1H,J=7.8 Hz), 7.24-7.30 (m,2H), 6.95-7.01 (m1H), 4.27 (s,2H). MS calcd. 200.1; MS (M+1) 201.1.

Workup

  1. additionTo the solution was added
  2. customMost of the methanol was evaporated under reduced pressure
  3. additionIce water was added to the residue
  4. filtrationIt was filtered
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-940fae32ff8e4a0fb3101fd3edf22eee
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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