Nicotinic Acid → HCID 532685, compound

HRID 129913Notes

Reaction equation

HRID 129913 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12](O)[CH:11]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[C:1]([O:9][C:12]1[CH:11]=[CH:10][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 9804-NitrophenolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 532685HCID 532685, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 9.85 g, 80 mmoles, nicotinic acid and 13.35 g, 96 =moles p-nitrophenol in 250 ml DMF was added 16.5 g, 80 mmoles DCC with stirring in ice-bath. After 1 hour at 0° C. and 3 hours at room temperature the urea was filtered off and the product was precipitated by the addition of an equal volume of water. Filtration, drying in vacuo and recrystallization from i-PrOH gave 11.22 g, 57% of white needles, m.p. 172.5°-173° C. (24)

Workup

  1. filtration3 hours at room temperature the urea was filtered off
  2. customthe product was precipitated by the addition of an equal volume of water
  3. filtrationFiltration
  4. dry with materialdrying in vacuo and recrystallization from i-PrOH

Sources & evidence

ORD record
ord-80c09076a87341378345b05d449aa6fd
Source dataset
uspto-grants-1995_11
Patent number
US05470947

Reaction notes

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