Quinoline → Propylamine

HRID 493115Notes

Reaction equation

HRID 493115 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[N:32]1C2C(=CC=CC=2)[CH:35]=[CH:34][CH:33]=1>P(Cl)(Cl)(Cl)=O.N1C=CC=CC=1>[NH2:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:33]([NH2:32])[CH2:34][CH3:35]

Participants

8

Reactant 4

HCID 7047QuinolineHCID 31297Methanesulfonyl chlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 178516432HCID 178516432, compound

Product 2

HCID 7852PropylamineHCID 5893541,5-Naphthyridin-4-amine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

4-Hydroxy-1,5-naphthyridines can be prepared from 3-aminopyridine derivatives by reaction with diethyl ethoxymethylene malonate to produce the 4-hydroxy-3-carboxylic acid ester derivative with subsequent hydrolysis to the acid, followed by thermal decarboxylation in quinoline (as for example described for 4-Hydroxy-[1,5]naphthyridine-3-carboxylic acid, J. T. Adams et al., J. Amer. Chem. Soc., 1946, 68, 1317). A 4-hydroxy-[1,5]naphthyridine can be converted to the 4-chloro derivative by heating in phosphorus oxychloride, or to the 4-methanesulphonyloxy or 4-trifluoromethanesulphonyloxy derivative by reaction with methanesulphonyl chloride or trifluoromethanesulphonic anhydride, respectively, in the presence of an organic base. A 4-amino 1,5-naphthyridine can be obtained from the 4-chloro derivative by reaction with n-propylamine in pyridine.

Workup

  1. customwith subsequent hydrolysis to the acid

Sources & evidence

ORD record
ord-792fbb81b1704bf3802137e15e62a9dd
Source dataset
uspto-grants-2009_05
Patent number
US07534793B2

Reaction notes

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