Picolinic acid → HCID 10402053, compound

HRID 2111966Notes

Reaction equation

HRID 2111966 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.[NH2:34][C:35]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:36]=1[C:37]([OH:39])=[O:38]>C1(C)C=CC=CC=1.C1COCC1>[Cl:44][C:42]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([NH:34][C:32]([NH:29][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:17])[CH:43]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 8471Triethylamine2×HCID 666462-Amino-4-chlorobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 10402053HCID 10402053, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridine-2-carboxylic acid (369 mg, 3 mmol) was suspended in 15 ml dry toluene and diphenyl-phosphoryl azide (958 mg, 3.5 mmol) added. Triethylamine (354 mg, 3.6 mmol) was then added drop-wise and the mixture stirred at room temperature for 0.5 hour. The solution was heated to 80° C. and after 2 hours 2-amino-4-chloro-benzoic acid (463 mg, 2.7 mmol) was added in 20 ml THF and triethylamine (0.354 g, 3.6 mmol) was also added. The mixture was stirred for 1 hour at 80° C. and then at room temperature overnight. The mixture was allowed to cool and the solvent was removed under reduced pressure. The residue was taken up into ethyl acetate and precipitated with heptane and filtered with suction. Yield after recrystallation from ethyl acetate/heptane was 640 mg (73%) of white crystalline solid (m.p. 222-224° C.).

Workup

  1. stirringThe mixture was stirred for 1 hour at 80° C.
  2. customat room temperature
  3. customovernight
  4. temperatureto cool
  5. customthe solvent was removed under reduced pressure
  6. customprecipitated with heptane
  7. filtrationfiltered with suction
  8. customYield after recrystallation from ethyl acetate/heptane

Sources & evidence

ORD record
ord-357f062ebe384ecebd50d608f4b7937f
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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