Hydrogen Bromide → 1,5-Naphthyridin-4-amine

HRID 513751Notes

Reaction equation

HRID 513751 reaction equation
Br.COC1C=CC(C[NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[N:13]=[CH:12][CH:11]=2)=CC=1.C([O-])(O)=O.[Na+]>>[NH3:9].[N:13]1[C:14]2[C:19](=[N:18][CH:17]=[CH:16][CH:15]=2)[C:10]([NH2:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 68183180(4-Methoxy-benzyl)-[1,5]naphthyridin-4-yl-amine

Product 2

HCID 222AmmoniaHCID 5893541,5-Naphthyridin-4-amineYield 183.2%

Conditions

Temperature
80 °C

Procedure

48% HBr (13 ml) was added to (4-methoxy-benzyl)-[1,5]naphthyridin-4-yl-amine 485 (0.5 g, 1.88 mmol) and the mixture was heated at 80° C. for 2 h. After cooling, the mixture was neutralized with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc (80 ml). The organic phase was washed with water, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH/Aq. NH3 (97:2:1) as the eluent to give the title compound (0.25 g, 90%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc (80 ml)
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM/MeOH/Aq

Sources & evidence

ORD record
ord-1c2a075070054a5a80d59412cb89a2be
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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