Picolinic acid → HCID 14390489, compound

HRID 1709394Notes

Reaction equation

HRID 1709394 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.[CH2:14]([O:16][C:17](=[O:29])[CH2:18][NH:19][C:20]1[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][N:21]=1)[CH3:15]>C1C=CC=CC=1.O1CCCC1>[CH2:14]([O:16][C:17](=[O:29])[CH2:18][NH:19][C:20]1[C:25]([NH:26][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:24][CH:23]=[CH:22][N:21]=1)[CH3:15]

Participants

6

Reactant 3

HCID 1018Picolinic acidHCID 24386Thionyl ChlorideHCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Product 1

HCID 14390489HCID 14390489, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (0.30 mole) and a solution of freshly prepared acid chloride of 2-pyridine carboxylic acid (0.150 mole), obtained by heating at reflux 2-pyridine carboxic acid and excess thionyl chloride in benzene and then azeotropic distillation with benzene, in dry tetrahydrofuran (50 ml) were added simultaneously (dropwise) to a stirred and chilled (10°-20° C.) solution of freshly prepared N-(3-amino-2-pyridinyl)glycine ethyl ester prepared by reducing N-(3-nitro-2-pyridinyl)glycine ethyl ester (0.106 mole) in 200 ml of dry tetrahydrofuran. The reaction mixture was stirred overnight at room temperature and was filtered. The filtrate was concentrated in vacuo and dissolved in ethyl acetate (250 ml). The solution was washed with saturated sodium bicarbonate solution (3×75 ml), water (2×75 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was crystallized from isopropyl ether-tetrahydrofuran giving 26.5 g (83%). A 3.0-g sample was twice recrystallized from isopropyl ether-tetrahydrofuran to give 2.4 g of a white needles, mp 98°-100° C.

Workup

  1. temperatureby heating
  2. distillationazeotropic distillation with benzene
  3. additionin dry tetrahydrofuran (50 ml) were added simultaneously (dropwise) to
  4. temperaturechilled (10°-20° C.) solution of freshly prepared N-(3-amino-2-pyridinyl)glycine ethyl ester
  5. customprepared
  6. stirringThe reaction mixture was stirred overnight at room temperature
  7. filtrationwas filtered
  8. concentrationThe filtrate was concentrated in vacuo
  9. dissolutiondissolved in ethyl acetate (250 ml)
  10. washThe solution was washed with saturated sodium bicarbonate solution (3×75 ml), water (2×75 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated in vacuo
  13. customThe residue was crystallized from isopropyl ether-tetrahydrofuran giving 26.5 g (83%)
  14. customA 3.0-g sample was twice recrystallized from isopropyl ether-tetrahydrofuran

Sources & evidence

ORD record
ord-b306f43a8d0749c58098307e8eb619ba
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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