Morpholine → 8-Morpholino-1,7-naphthyridin-6-amine

HRID 542714Notes

Reaction equation

HRID 542714 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Br)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CO>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 8083MorpholineHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 139243758-Morpholino-1,7-naphthyridin-6-amineYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 800 mg of 6-amino-8-bromo-1,7-naphthyridine and 3.12 g of morpholine, 40 ml of methanol was added. The resultant mixture was refluxed for 13 hours. After the reaction, methanol was distilled off under reduced pressure and chloroform was added to the residue. After washing the chloroform solution with water, it was dried with anhydrous magnesium sulfate. Chloroform was distilled off under reduced pressure and a small amount of acetone was added to the residue to dissolve same. Hexane was then added to the residue, followed by removal of insoluble matter by filtration. The filtrate was concentrated and the residue was recrystallized from a mixed solvent of chloroform and hexane, thereby obtaining 500 mg of 6-amino-8-morpholino-1,7-naphthyridine (Compound No. 3) as yellowish crystals (yield: 60.9%).

Workup

  1. additionwas added
  2. distillationwas distilled off under reduced pressure and chloroform
  3. additionwas added to the residue
  4. washAfter washing the chloroform solution with water, it
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. distillationChloroform was distilled off under reduced pressure
  7. additiona small amount of acetone was added to the residue
  8. dissolutionto dissolve same
  9. additionHexane was then added to the residue
  10. customfollowed by removal of insoluble matter by filtration
  11. concentrationThe filtrate was concentrated
  12. customthe residue was recrystallized from a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-fb21fdfa382a4550896f83757074d6e3
Source dataset
uspto-grants-1987_04
Patent number
US04659710

Reaction notes

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