Nitric Acid → 1-[4-(6-Chloro-3-nitropyridin-2-yl)piperazin-1-yl]ethan-1-one

HRID 2413120Notes

Reaction equation

HRID 2413120 reaction equation
ClC1C=CC=C(Cl)N=1.[N+]([O-])(O)=O.S(=O)(=O)(O)O.Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([Cl:28])[N:20]=1.[C:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)(=[O:31])[CH3:30]>C(Cl)(Cl)Cl>[C:29]([N:32]1[CH2:37][CH2:36][N:35]([C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([Cl:28])[N:20]=2)[CH2:34][CH2:33]1)(=[O:31])[CH3:30]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 169892,6-DichloropyridineHCID 837951-AcetylpiperazineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 132907561-[4-(6-Chloro-3-nitropyridin-2-yl)piperazin-1-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2,6-Dichloropyridine is nitrated with fuming nitric acid and concentrated sulfuric acid. The product, 2,6-dichloro-3-nitropyridine, is allowed to react with N-acetyl-piperazine in chloroform to give 2-(4-acetyl-1-piperazinyl)-6-chloro-3-nitropyridine (m.p. 137°-138° C.). The compound obtained is treated with aqueous ammoniaethanol in an autoclave to give 2-(4-acetyl-1-piperazinyl)-6-amino-3-nitropyridine (m.p. 202°-203° C.), which is then acetylated with acetic anhydride in acetic acid to give 6-acetylamino-2-(4-acetyl-1-piperazinyl)-3-nitropyridine (m.p. 189°-193° C., 221°-223° C.).

Sources & evidence

ORD record
ord-c9b3a2e9864245f9975bd1b405c59904
Source dataset
uspto-grants-1985_01
Patent number
US04496566

Reaction notes

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