p-Toluenesulfonic acid → HCID 43112089, compound

HRID 392425Notes

Reaction equation

HRID 392425 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[NH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>CO>[CH3:17][O:16][C:14]([C:13]1[CH:18]=[CH:19][C:10]([NH:9][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:11][CH:12]=1)=[O:15]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 103713-PyridinecarboxaldehydeHCID 12082Methyl 4-aminobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 43112089HCID 43112089, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Alternately, 3-pyridinecarboxaldehyde ((61.6 g, 0.575 moles, 1 eq) and methyl 4-aminobenzoate (1-03.87 g, 0.687 moles, 1.2 eq) with p-toluenesulfonic acid (2.19 g, 0.012 moles, 0.02 eq) were refluxed in methanol (25 volumes) for 2 hours. The reaction mixture was cooled to 0° C. and sodium borohydride (67.6 g, 1.787 moles, 3.5 eq) added slowly then it was allowed to warm to ambient overnight. The reaction was concentrated, dissolved with dichloromethane and washed with water then brine, and evaporated to give the title compound.

Workup

  1. temperatureto warm to ambient overnight
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved with dichloromethane
  4. washwashed with water
  5. custombrine, and evaporated

Sources & evidence

ORD record
ord-ab2c64dc8c3c46dc810e604074eaf9f4
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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