Quinoline → Propylamine

HRID 394498Notes

Reaction equation

HRID 394498 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.[N:12]1C2C(=CC=CC=2)[CH:15]=[CH:14][CH:13]=1>P(Cl)(Cl)(Cl)=O.N1C=CC=CC=1>[NH2:12][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:13]([NH2:12])[CH2:14][CH3:15]

Participants

6

Reactant 2

HCID 7047QuinolineHCID 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, Joe 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. 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-f404d6bf03a142acb3c462ebf790b17d
Source dataset
uspto-grants-2003_08
Patent number
US06602882B1

Reaction notes

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