4-Nitrophenol → p-nitrophenyl picolinate

HRID 2107758Notes

Reaction equation

HRID 2107758 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].[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>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9][C:12]1[CH:11]=[CH:10][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1018Picolinic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 698410p-nitrophenyl picolinateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.92 g, 40 mmoles, picolinic acid and 5.84 g, 42 mmoles p-nitrophenol were suspended/dissolved in 200 ml CH2Cl2. Then 8.24 g, 40 mmoles, DCC was added in 20 ml CH2Cl2 with vigorous stirring. Stirring was continued in room temperature for 17 h. Then the mixture was filtered and the filter cake washed with 30-40 ml CH2Cl2. The raw product was first treated with 100 ml Et2O with stirring in ice-bath and filtered. Recrystallization from 250 ml iPrOH gave 6.24 g, 63% product. M.p. 154°-6° C. (dec.). M.p. (Fife and Przystas, loc. cit.) 145°-7° C. Anal. C,H,N,O.

Workup

  1. filtrationThen the mixture was filtered
  2. washthe filter cake washed with 30-40 ml CH2Cl2
  3. additionThe raw product was first treated with 100 ml Et2O
  4. stirringwith stirring in ice-bath
  5. filtrationfiltered
  6. customRecrystallization from 250 ml iPrOH

Sources & evidence

ORD record
ord-fe18b5791bb54b27be0b8e818cbd8003
Source dataset
uspto-grants-1990_06
Patent number
US04935491

Reaction notes

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