Fusaric Acid → 3-Fluoro-4cyanophenyl 5-n-butylpicolinate

HRID 542691

Reaction equation

HRID 542691 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[F:14][C:15]1[CH:16]=[C:17](O)[CH:18]=[CH:19][C:20]=1[C:21]#[N:22].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13][C:17]2[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[C:15]([F:14])[CH:16]=2)=[O:12])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3442Fusaric AcidHCID 10868DicyclohexylcarbodiimideHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 137098973-Fluoro-4cyanophenyl 5-n-butylpicolinateYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-n-butyl picolinic acid (1.8 g) and 3-fluoro-4-cyanophenol (1.4 g) were dissolved in methylene chloride (30 ml). While the resulting solution was kept at 0° C. or lower, a solution (20 ml) of dicyclohexylcarbodimide (2.1 g) in methylene chloride was dropped to the above solution, followed by further agitating for 3 hours, filtering off the resulting solids, adding 2N-NaOH aqueous solution to the filtrate, separating the methylene chloride layer, washing it with water till the washing water became neutral, distilling off the solvent from the methylene chloride layer and recrystallizing the residue from ethanol to obtain the objective 3-fluoro-4cyanophenyl 5-n-butylpicolinate (0.3 g) having a m.p. of 45.1°-46.1° C.

Workup

  1. customwas kept at 0° C.
  2. filtrationfiltering off the resulting solids
  3. additionadding 2N-NaOH aqueous solution to the filtrate
  4. customseparating the methylene chloride layer
  5. washwashing it with water till the washing water
  6. distillationdistilling off the solvent from the methylene chloride layer
  7. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-4271be2515944a68886db3f4397c44fb
Source dataset
uspto-grants-1987_04
Patent number
US04659500

Linked notes

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