2-Aminopyrimidine → 2-Aminopyridine

HRID 1758133Notes

Reaction equation

HRID 1758133 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH2:11]C1N=CC=CN=1>>[NH2:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 783082-Chloro-5-nitropyridine

Product 2

HCID 104392-AminopyridineHCID 778882-Amino-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-25585783180a44ba800a7b6bf00276d2
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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