Ammonia → HCID 13151383, compound

HRID 851276Notes

Reaction equation

HRID 851276 reaction equation
[NH3:1].F[C:3]1[C:8]([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:7][CH:6]=[C:5]([F:16])[N:4]=1.O>C(N)=O>[NH2:1][C:3]1[C:8]([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:7][CH:6]=[C:5]([F:16])[N:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 13151382HCID 13151382, compound

Product 1

HCID 13151383HCID 13151383, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

To a mechanically stirred solution of ammonia (14 grams (g)) in formamide (300 milliliter (ml)) was added all at once butyl 2,6-difluoropyridine-3-carboxylate (29 g, 0.135 mole). The resulting mixture was stirred overnight at room temperature. The mixture was then poured into water (1500 ml) and the product was filtered. After washing with several portions of water, the solid was dissolved in chloroform, dried (MgSO4) and the solvent evaporated. The resulting solid (26 g, m.p.=84°-120° C.) was separated via preparative high pressure liquid chromatography (8:2 hexane-acetone) to give first the desired butyl 2-amino-6-fluoropyridine-3-carboxylate (10 g) which after recrystallization from hexane had a m.p.=88.5°-90.5° C. Eluting second was the isomeric butyl 6-amino-2-fluoropyridine-3-carboxylate (9 g) which after recrystallization from toluene had a m.p.=132.5°-134° C.

Workup

  1. filtrationthe product was filtered
  2. washAfter washing with several portions of water
  3. dissolutionthe solid was dissolved in chloroform
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customThe resulting solid (26 g, m.p.=84°-120° C.) was separated via preparative high pressure liquid chromatography (8:2 hexane-acetone)

Sources & evidence

ORD record
ord-5a215d36b55f4e6c9f11e5bb75916eec
Source dataset
uspto-grants-1983_05
Patent number
US04383851

Reaction notes

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