Propylamine hydrochloride → 6-Methoxy-1,5-naphthyridin-4-amine

HRID 456579

Reaction equation

HRID 456579 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.Cl.C([NH2:25])CC>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH2:25]

Participants

4

Reactant 2

HCID 11165Propylamine hydrochlorideHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Product 1

HCID 114352366-Methoxy-1,5-naphthyridin-4-amineYield 91.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of triflate (b) (25 g, 81.2 mmol) and propylamine hydrochloride (47 g, 487 mmol) in pyridine (300 ml) was heated to reflux overnight. The mixture was evaporated to dryness, dissolved in 0.5M aqueous hydrochloric acid (400 ml) and extracted three times with dichloromethane. The aqueous phase was then basified with 40% aqueous sodium hydroxide solution and extracted twice with dichloromethane. Drying and evaporation afforded a buff coloured solid (13.0 g, 90%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe mixture was evaporated to dryness
  4. dissolutiondissolved in 0.5M aqueous hydrochloric acid (400 ml)
  5. extractionextracted three times with dichloromethane
  6. extractionextracted twice with dichloromethane
  7. customDrying
  8. customevaporation

Sources & evidence

ORD record
ord-3162b2c3d3954e30bf5f676d9b6d0ff6
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Linked notes

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