3-Pyridinecarboxaldehyde → HCID 22036171, compound

HRID 1789654Notes

Reaction equation

HRID 1789654 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](C=O)[CH:11]=1.[C:18](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[CH2:18][NH:7][C:6]1[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 660384-(Methylthio)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22036171HCID 22036171, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.0 mL (16.07 mmol) of 4-(methylthio)aniline dissolved in 25 mL dichloromethane was added 1.52 mL (16.07 mmol) 3-pyridinecarboxaldehyde, followed by 5.11 g (24.11 mmol) sodium triacetoxyborohydride. The mixture was stirred at room temperature for 4 h, partitioned between EtOAc and brine, dried over MgSO4 and concentrated. Column chromatography, eluting with ethyl acetate/hexane, provided 3.70 g of 4-[(pyridin-2-ylmethyl)amino]thioanisole, pure by 1H NMR.

Workup

  1. custompartitioned between EtOAc and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. washColumn chromatography, eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-9a4faf2fd423406690350473b80690da
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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