HCID 86601069, compound → 2-Chloro-5-nitropyridine

HRID 1758134Notes

Reaction equation

HRID 1758134 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].P(Cl)(Cl)(Cl)=O>>[Cl:12][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 86601069HCID 86601069, compoundHCID 178526703HCID 178526703, compound2×

Product 1

HCID 783082-Chloro-5-nitropyridine

Procedure

Alternatively, 2-chloro-5-nitropyridine can be prepared using the procedure described in the Journal Chemical Society 9 (1941), starting with 2-aminopyrimidine. Nitration of 2-aminopyridine gives 2-amino-5-nitropyridine, which can be converted into 2-hydroxy-5-nitropyridine by a diazonium reaction. Subsequent heating of 2-hydroxy-5-nitropyridine in a phosphorous pentachloride/phosphorous oxychloride mixture yields 2-chloro-5-nitropyridine. The synthesis is summarized below: ##STR13##

Sources & evidence

ORD record
ord-1e83d46b95554d568ff9b37ceb33ab07
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

Loading…