Sodium Hydroxide → 1-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)methanamine

HRID 1057503Notes

Reaction equation

HRID 1057503 reaction equation
Cl.O[NH2:3].CC([O-])=O.O.O.O.[Na+].[NH:12]1[C:17]2=[N:18][C:19]([CH:22]=O)=[CH:20][CH:21]=[C:16]2[CH2:15][CH2:14][CH2:13]1.[OH-].[Na+]>CO.O.FC(F)(F)C(O)=O.[Zn].C(Cl)Cl>[NH:12]1[C:17]2=[N:18][C:19]([CH2:22][NH2:3])=[CH:20][CH:21]=[C:16]2[CH2:15][CH2:14][CH2:13]1

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehydeHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 179406661-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)methanamine

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

Hydroxyamine hydrochloride (2 eq), sodium acetatetrihydrate (2 eq) and water (0.4M) were heated at 60° C. 1,2,3,4-tetrahydropyridino[2,3-b]pyridine-7-carbaldehyde was dissolved in methanol (2.5 mL) and added to the resulting solution. Additional methanol was added until the solution became clear, the reaction was stirred at 60° C. for 18 hrs. The mixture was cooled to room temperature, diluted with water (25 mL) and extracted with ether. The organic layer was extracted with saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated by in vacuo. To a solution of the oxime in trifluoroacetic acid (5 mL) was added zinc dust (5.6 eq) in several portions, while keeping the temperature between 15-25° C. After stirring for 15 mins., the mixture was added to a solution of an aqueous 2N NaOH (39 mL) solution and methylene chloride (21 mL) at 0° C. and stirred for an additional 15 mins. The reaction was filtered and the organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated in vacuo to yield the product. EI-MS m/z 163(M+H)+.

Workup

  1. additionadded to the resulting solution
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ether
  4. extractionThe organic layer was extracted with saturated sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by in vacuo
  8. custombetween 15-25° C
  9. stirringAfter stirring for 15 mins
  10. stirringstirred for an additional 15 mins
  11. filtrationThe reaction was filtered
  12. customthe organic layer was separated
  13. washwashed with water and brine
  14. dry with materialdried over sodium sulfate
  15. concentrationconcentrated in vacuo
  16. customto yield the product

Sources & evidence

ORD record
ord-a2aedc3976da4af5ad4fe135f0ee85f5
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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