Phosphorus oxybromide → 4-BroMo-1,6-naphthyridine

HRID 542508Notes

Reaction equation

HRID 542508 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:14])=O.O=P(Cl)(Cl)[Cl:19]>>[Br:14][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 24813Phosphorus oxychlorideHCID 178516446HCID 178516446, compound

Product 2

HCID 125201424-BroMo-1,6-naphthyridineHCID 217666944-Chloro-1,6-naphthyridine

Procedure

Paudler et al., J. Heterocyclic Chem. 2 (4), 393-8 (1965), show the synthesis and NMR spectra of various 4-substituted-1,6-naphthyridines, for example, the reaction of 4-hydroxy-1,6-naphthyridine with POBr3 or POCl3 to obtain 4-bromo-1,6-naphthyridine or 4-chloro-1,6-naphthyridine, respectively. Also shown is the reaction of 4-bromo-1,6-naphthyridine with dimethylamine to produce 4-dimethylamino-1,6-naphthyridine and the reaction 4-chloro-1,6-naphthyridine with piperidine or hydrazine to produce 4-(1-piperidinyl)-1,6-naphthyridine or 4-hydrazino-1,6-naphthyridine, respectively.

Sources & evidence

ORD record
ord-db44232d870b4ee992d7c2286c8055a6
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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