Ammonia → HCID 13151408, compound

HRID 851277Notes

Reaction equation

HRID 851277 reaction equation
[NH3:1].[F:2][C:3]1[C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=[C:5](F)[N:4]=1>C(N)=O>[NH2:1][C:5]1[N:4]=[C:3]([F:2])[C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20501992HCID 20501992, compound

Product 1

HCID 13151408HCID 13151408, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

To a stirred solution of ammonia (15 g) in formamide (250 ml) was added all at once benzyl 2,6-difluoropyridine-3-carboxylate (20 g, 0.08 mole). The mixture slowly became homogeneous, then a solid began to separate. After two hours, the mixture was poured into water (1000 ml) and the solid filtered. The solid was washed with several portions of water then air dried. Continuous extraction for one hour via a Soxhlet extraction apparatus using hexane as the solvent gave, after concentrating to 250 ml and cooling, 6.0 g (30%) of the desired benzyl 2-amino-6-fluoropyridine-3-carboxylate: m.p.=92°-94° C. The hexane insoluble material was recrystallized from a small volume of acetone to give 5.5 g (28%) of the isomeric benzyl 6-amino-2-fluoropyridine-3-carboxylate: m.p.=157.5°-159.5° C.

Workup

  1. customto separate
  2. additionthe mixture was poured into water (1000 ml)
  3. filtrationthe solid filtered
  4. washThe solid was washed with several portions of water
  5. customair dried
  6. extractionContinuous extraction for one hour
  7. extractionvia a Soxhlet extraction apparatus
  8. customgave
  9. concentrationafter concentrating to 250 ml
  10. temperaturecooling
  11. customThe hexane insoluble material was recrystallized from a small volume of acetone

Sources & evidence

ORD record
ord-b742a7aeaa3d488897d7f6102eb1b21d
Source dataset
uspto-grants-1983_05
Patent number
US04383851

Reaction notes

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