Propylamine hydrochloride → 4-Amino-2-methyl-[1,5]-naphthyridine

HRID 1358253Notes

Reaction equation

HRID 1358253 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.Cl.C([NH2:24])CC>N1C=CC=CC=1>[NH2:24][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1

Participants

4

Reactant 2

HCID 11165Propylamine hydrochlorideHCID 21137487Trifluoromethane Sulfonic Acid 2-Methyl-[1,5]naphthyridin-4-yl Ester

Product 1

HCID 112866094-Amino-2-methyl-[1,5]-naphthyridineYield 110.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

D1 (2.2 g) and n-propylamine hydrochloride (2.34 g) were combined in pyridine (75 ml) and the mixture refluxed for 8 h. Solvent was removed at reduced pressure, the residue dissolved in 2N sodium hydroxide and extracted with diethyl ether (×3) and DCM (×2). The combined organic phase was dried (Na2SO4) and solvent removed at reduced pressure. The residue was triturated with pentane to give the title compound (1.32 g) as a pale orange solid. 1H NMR (CDCl3) δ: 2.60 (3H, s), 5.44 (2H, bs), 6.66 (1H, s), 7.54 (1H, dd), 8.17 (1H, dd), 8.67 (1H, m).

Workup

  1. temperaturethe mixture refluxed for 8 h
  2. customSolvent was removed at reduced pressure
  3. dissolutionthe residue dissolved in 2N sodium hydroxide
  4. extractionextracted with diethyl ether (×3) and DCM (×2)
  5. dry with materialThe combined organic phase was dried (Na2SO4) and solvent
  6. customremoved at reduced pressure
  7. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-a8e5a058982646cdbda6c968ae5cdaf4
Source dataset
uspto-grants-2003_07
Patent number
US06596730B1

Reaction notes

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