Synthesis and properties of 5-chloro-4-nitropyrazoles

Article abstract of DOI:10.1134/S1070428006060157

The nitration of 5-chloropyrazoles with a mixture of 100% nitric acid and 65% oleum or a mixture of 60% nitric acid and polyphosphoric acid gave substituted 5-chloro-4-nitropyrazoles in 45-91% yield. The nitration of 3-aryl-5-halopyrazoles was accompanied

Full text of DOI:10.1134/S1070428006060157

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ꢂ+ꢈS\UD]ROHꢅꢃ ꢁꢊꢂꢋꢃ POꢃ RIꢃ QLWULFꢃ DFLGꢃ ꢌGꢃ ꢃ ꢂꢊꢇꢂꢃ JꢑFP ꢍꢃ SKRVSKRULFꢃ DFLGꢏꢃ WKHꢃ UHDFWLRQꢃ P L[WXUHꢃ ZDVꢃ KHDWHGꢃ IRUꢃꢃ
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KHDWHGꢃIRUꢃꢐꢃKꢃDWꢃꢂꢆꢁƒ&ꢊꢃ<LHOGꢃꢁꢊꢉꢂꢃJꢃꢌꢐꢂ#ꢍꢅꢃPSꢃꢇꢋƒ&ꢊꢃ WUXPꢅꢃ ꢅꢃFP ꢓꢃꢆꢀꢇꢇꢅꢃꢆꢀꢆꢇꢅꢃꢆꢐꢇꢇꢃꢌ&±+ꢍꢏꢃꢂꢇꢋꢁꢅꢃꢂꢋꢇꢁꢃ
,5ꢃVSHFWUXPꢅꢃ ꢅꢃFP ꢓꢃꢆꢀꢒꢇꢅꢃꢆꢀꢋꢁꢅꢃꢆꢐꢒꢁꢃꢌ&±+ꢍꢏꢃꢂꢇꢆꢇꢅꢃ ꢌ12 ꢍꢊꢃ +ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢉꢊꢂꢆꢃWꢃꢌꢆ+ꢅꢃ
ꢂꢋꢇꢁꢃꢌ12 ꢍꢊꢃ +ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢋꢊꢐꢇꢃ &+ ꢅꢃ-ꢃ ꢃꢒꢊꢉꢃ+]ꢍꢅꢃꢆꢊꢇꢋꢃꢌꢋ+ꢅꢃ&+ ꢍꢅꢃꢂꢊꢐꢋꢃPꢃꢌꢆ+ꢅꢃ&+ ꢍꢅꢃ
ꢌ&+ ꢍꢅꢃꢋꢊꢇꢒꢃPꢃꢌꢂ+ꢅꢃ&+ꢅꢃ-ꢃ ꢃꢄꢊꢀꢃ+]ꢍꢅꢃꢂꢊꢆꢐꢃGꢃꢌꢄ+ꢅꢃꢆ&+ ꢅꢃ ꢂꢊꢆꢀꢃPꢃꢌꢐ+ꢅꢃꢉ&+ ꢍꢅꢃꢁꢊꢐꢄꢃWꢃꢌꢋ+ꢅꢃ&+ ꢅꢃ-ꢃ ꢃꢒꢊꢉꢃ+]ꢍꢊꢃꢃ
-ꢃ ꢃꢄꢊꢀꢃ+]ꢍꢊꢃ &ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃ
&ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢂꢉꢄꢊꢇꢐꢃꢌ& ꢍꢅꢃ
ꢂꢇꢇꢊꢁꢇꢃꢌ& ꢍꢅꢃꢂꢋꢐꢊꢀꢐꢃꢌ& ꢍꢅꢃꢂꢆꢐꢊꢆꢒꢃꢌ& ꢍꢅꢃꢋꢒꢊꢂꢆꢃꢌ&+ ꢍꢅꢃ ꢂꢆꢒꢊꢉꢇꢃ ꢌ& ꢍꢅꢃ ꢇꢁꢊꢁꢒꢃ ꢌ&+ ꢍꢅꢃ ꢋꢂꢊꢇꢒꢃ ꢌ&+ ꢍꢅꢃ ꢆꢀꢊꢂꢋꢃ ꢌ&+ ꢍꢅꢃ
ꢆꢒꢊꢉꢆꢃꢌ&+ꢍꢅꢃꢆꢂꢊꢁꢂꢃꢌꢆ&+ ꢍꢊꢃ)RXQGꢅꢃ#ꢓꢃ&ꢃꢉꢂꢊꢆꢇꢏꢃ+ꢃꢇꢊꢁꢂꢏꢃ ꢆꢐꢊꢄꢀꢃꢌ&+ ꢍꢅꢃꢆꢄꢊꢋꢂꢃꢌ&+ ꢍꢅꢃꢆꢆꢊꢇꢆꢃꢌ&+ ꢍꢅꢃꢂꢉꢊꢒꢁꢃꢌ&+ ꢍꢅꢃ
&Oꢃꢂꢒꢊꢋꢐꢏꢃ1ꢃꢆꢁꢊꢄꢂꢊꢃ& + &O1 2 ꢊꢃ&DOFXODWHGꢅꢃ#ꢓꢃꢃ ꢂꢋꢊꢀꢇꢃꢌ&+ ꢍꢊꢃ)RXQGꢅꢃ#ꢓꢃ&ꢃꢇꢁꢊꢐꢉꢏꢃ+ꢃꢒꢊꢁꢋꢏꢃ&Oꢃꢂꢋꢊꢄꢋꢏꢃꢃ
1ꢃꢂꢄꢊꢂꢄꢊꢃ& + &O1 2 ꢊꢃ&DOFXODWHGꢅꢃ#ꢓꢃ&ꢃꢇꢁꢊꢐꢒꢏꢃꢃ
+ꢃꢄꢊꢀꢀꢏꢃ&Oꢃꢂꢋꢊꢄꢇꢏꢃ1ꢃꢂꢄꢊꢂꢐꢊꢃ
&ꢃꢉꢂꢊꢆꢀꢏꢃ+ꢃꢉꢊꢀꢇꢏꢃ&Oꢃꢂꢒꢊꢉꢂꢏꢃ1ꢃꢆꢁꢊꢄꢉꢊꢃ
ꢀꢁ&KORURꢁꢆꢁHWK\OꢁꢈꢁPHWK\OꢁꢂꢁQLWURꢁꢆ+ꢁS\UD]ROH
ꢉ;,,ꢊꢃꢃDꢁꢃ&RPSRXQGꢃ;,,ꢃZDVꢃV\QWKHVL]HGꢃDVꢃGHVFULEHGꢃ
ꢀꢁ&KORURꢁꢆꢁKHSW\OꢁꢂꢁQLWURꢁꢈꢁWULIOXRURPHWK\Oꢁꢆ+ꢁ
DERYHꢃ IRUꢃ QLWURS\UD]ROHꢃ ,;ꢃ IURP ꢃ ꢁꢊꢇꢐꢃ Jꢃ ꢌꢉꢃ P P ROꢍꢃ RIꢃ S\UD]ROH ꢉ;9ꢊꢃZDVꢃV\QWKHVL]HGꢃDFFRUGLQJꢃWRꢃPHWKRGꢃEꢃ
FRPSRXQGꢃ,9ꢅꢃꢆꢊꢂꢃPOꢃRIꢃQLWULFꢃDFLGꢃꢌGꢃ ꢃꢂꢊꢇꢂꢃJꢑFP ꢍꢅꢃ IURPꢃꢁꢊꢋꢋꢃJꢃꢌꢂꢃPPROꢍꢃRIꢃꢇꢈFKORURꢈꢂꢈKHSW\OꢈꢋꢈWULIOXRURꢈ
5866,$1ꢃꢃ-2851$/ꢃꢃ2)ꢃꢃ25*$1,&ꢃꢃ&+(0,675<ꢃꢃꢃ9ROꢊꢃꢃꢉꢆꢃꢃꢃ1Rꢊꢃꢃꢄꢃꢃꢃꢆꢁꢁꢄꢃ

6<17+(6,6ꢃꢃ$1'ꢃꢃ3523(57,(6ꢃꢃ2)ꢃꢃꢇꢈ&+/252ꢈꢉꢈ1,7523<5$=2/(6ꢃ
ꢀꢁꢇꢃ
PHWK\Oꢈꢂ+ꢈS\UD]ROHꢅꢃ ꢋꢃ Jꢃ RIꢃ SRO\SKRVSKRULFꢃ DFLGꢅꢃ DQGꢃ
ꢁꢊꢆꢇꢃPOꢃRIꢃꢄꢁ#ꢃQLWULFꢃDFLGꢏꢃWKHꢃUHDFWLRQꢃPL[WXUHꢃZDVꢃ
KHDWHGꢃIRUꢃꢂꢂꢃKꢃDWꢃꢀꢇƒ&ꢊꢃ<LHOGꢃꢁꢊꢂꢋꢃJꢃꢌꢉꢇ#ꢍꢅꢃGDUNꢃYHU\ꢃ
YLVFRXVꢃVXEVWDQFHꢊꢃ,5ꢃVSHFWUXPꢅꢃ ꢅꢃFP ꢓꢃꢆꢀꢇꢁꢅꢃꢆꢀꢆꢁꢅꢃ
ꢆꢐꢇꢁꢃꢌ&±+ꢍꢏꢃꢂꢇꢋꢇꢅꢃꢂꢋꢇꢁꢃꢌ12 ꢍꢊꢃ +ꢃ105ꢃVSHFWUXPꢃ
ꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢉꢊꢆꢉꢃWꢃꢌꢆ+ꢅꢃ&+ ꢅꢃ-ꢃ ꢃꢒꢊꢇꢃ+]ꢍꢅꢃꢂꢊꢐꢐꢃPꢃ
ꢌꢆ+ꢅꢃ&+ ꢍꢅꢃꢂꢊꢆꢀꢃPꢃꢌꢐ+ꢅꢃꢉ&+ ꢍꢅꢃꢁꢊꢐꢄꢃWꢃꢌꢋ+ꢅꢃ&+ ꢅꢃ-ꢃ ꢃ
ꢒꢊꢇꢃ+]ꢍꢊꢃ)RXQGꢅꢃ#ꢓꢃ&ꢃꢉꢂꢊꢀꢇꢏꢃ+ꢃꢇꢊꢁꢂꢏꢃ&Oꢃꢂꢂꢊꢆꢇꢏꢃ)ꢃꢂꢒꢊꢐꢒꢏꢃ
1ꢃꢂꢇꢊꢆꢇꢊꢃ& + &O) 1 2 ꢊꢃ&DOFXODWHGꢅꢃ#ꢓꢃ&ꢃꢉꢆꢊꢂꢆꢏꢃꢃ
+ꢃꢉꢊꢐꢆꢏꢃ&Oꢃꢂꢂꢊꢋꢁꢏꢃ)ꢃꢂꢐꢊꢂꢒꢏꢃ1ꢃꢂꢋꢊꢋꢀꢊꢃ
ꢀꢁ&KORURꢁꢆꢁꢉꢇꢄꢂꢁGLQLWURSKHQ\OꢊꢁꢂꢁQLWURꢁꢈꢁSURS\Oꢁ
ꢆ+ꢁS\UD]ROH ꢉ;9,ꢊꢃꢃ Dꢊꢃ &RPSRXQGꢃ ;9,ꢃ ZDVꢃ V\QWKHꢈ
VL]HGꢃIURPꢃꢂꢊꢁꢉꢃJꢃꢌꢋꢊꢋꢃPPROꢍꢃRIꢃS\UD]ROHꢃ 9,,,ꢃXVLQJꢃ
ꢁꢊꢂꢇꢃPOꢃRIꢃQLWULFꢃDFLGꢃꢌGꢃ ꢃꢂꢊꢇꢂꢃJꢑFP ꢍꢃDQGꢃꢂꢊꢂꢇꢃPOꢃRIꢃ
ꢄꢇ#ꢃROHXPꢏꢃWKHꢃUHDFWLRQꢃPL[WXUHꢃZDVꢃKHDWHGꢃIRUꢃꢐꢃKꢃDWꢃ
ꢂꢆꢁƒ&ꢊꢃ7KHꢃSURGXFWꢃZDVꢃLVRODWHGꢃDVꢃDꢃZD[\ꢃPDWHULDOꢊꢃ
<LHOGꢃꢁꢊꢇꢋꢃJꢃꢌꢉꢇ#ꢍꢊꢃꢃ
Eꢁꢃ%\ꢃWUHDWPHQWꢃRIꢃꢁꢊꢆꢐꢃJꢃꢌꢁꢊꢀꢃPPROꢍꢃRIꢃꢇꢈFKORURꢈꢂꢈ
ꢌꢆꢅꢉꢈGLQLWURSKHQ\OꢍꢈꢋꢈSURS\Oꢈꢂ+ꢈS\UD]ROHꢃZLWKꢃꢁꢊꢆꢃJꢃRIꢃ
ꢄꢁ#ꢃ QLWULFꢃ DFLGꢃ LQꢃ ꢂꢊꢆꢇꢃ Jꢃ RIꢃ SRO\SKRVSKRULFꢃ DFLGꢃ DWꢃ
ꢂꢁꢁƒ&ꢃꢌUHDFWLRQꢃWLPHꢃꢋꢃKꢍꢃZHꢃREWDLQHGꢃꢁꢊꢆꢇꢃJꢃꢌꢒꢐ#ꢍꢃRIꢃ
FRPSRXQGꢃ;9,ꢊꢃ,5ꢃVSHFWUXPꢅꢃ ꢅꢃFP ꢓꢃꢋꢁꢀꢁꢃꢌ &±+ꢍꢏꢃ
ꢆꢀꢇꢇꢅꢃꢆꢀꢆꢇꢅꢃꢆꢐꢒꢇꢃꢌ&±+ ꢍꢏꢃꢂꢄꢁꢁꢃꢌ& 1ꢍꢏꢃꢂꢇꢆꢇꢅꢃꢂꢋꢉꢁꢃ
ꢌ12 ꢍꢊꢃ +ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢐꢊꢀꢐꢃGꢃ
ꢌꢂ+ꢅꢃꢋꢈ+ꢅꢃ -ꢃ ꢃꢆꢊꢋꢃ+]ꢍꢅꢃꢐꢊꢒꢁꢃGꢊGꢃꢌꢂ+ꢅꢃꢇꢎꢈ+ꢅꢃ -ꢃ ꢃꢆꢊꢋꢅꢃꢃ
-ꢃ ꢃꢐꢊꢒꢃ+]ꢍꢅꢃꢒꢊꢀꢋꢃGꢃꢌꢂ+ꢅꢃꢄꢎꢈ+ꢅꢃ -ꢃ ꢃꢐꢊꢒꢃ+]ꢍꢅꢃꢆꢊꢀꢄꢃWꢃꢌꢆ+ꢅꢃ
&+ ꢅꢃ-ꢃ ꢃꢒꢊꢉꢃ+]ꢍꢅꢃꢂꢊꢒꢋꢃPꢃꢌꢆ+ꢅꢃ&+ ꢅꢃ-ꢃ ꢃꢒꢊꢉꢃ+]ꢍꢅꢃꢁꢊꢀꢐꢃWꢃ
ꢌꢋ+ꢅꢃ &+ ꢅꢃ -ꢃ ꢃ ꢒꢊꢉꢃ+]ꢍꢊꢃ &ꢃ 105ꢃ VSHFWUXPꢃ ꢌ&'&O ꢍꢅꢃ
ꢅꢃSSPꢓꢃꢂꢇꢆꢊꢀꢁꢃꢌ& ꢍꢅꢃꢂꢉꢐꢊꢆꢐꢃꢌ& ꢍꢅꢃꢂꢉꢇꢊꢉꢆꢃꢌ& ꢍꢅꢃꢂꢋꢀꢊꢂꢂꢃ
ꢌ& ꢍꢅꢃ ꢂꢋꢉꢊꢉꢁꢃ ꢌ& ꢍꢅꢃ ꢂꢋꢂꢊꢂꢁꢃ ꢌ& ꢍꢅꢃ ꢂꢆꢀꢊꢐꢐꢃ ꢌ& ꢍꢅꢃ ꢂꢆꢐꢊꢆꢒꢃ
ꢌ& ꢍꢅꢃꢂꢆꢂꢊꢉꢋꢃꢌ& ꢍꢅꢃꢆꢀꢊꢀꢒꢃꢌ&+ ꢍꢅꢃꢆꢁꢊꢉꢄꢃꢌ&+ ꢍꢅꢃꢂꢋꢊꢉꢐꢃ
ꢌ&+ ꢍꢊꢃ)RXQGꢅꢃ#ꢓꢃ&ꢃꢉꢁꢊꢇꢁꢏꢃ+ꢃꢆꢊꢐꢇꢏꢃ&Oꢃꢂꢁꢊꢁꢏꢃ1ꢃꢂꢀꢊꢄꢇꢊꢃ
& + &O1 2 ꢊꢃ &DOFXODWHGꢅꢃ #ꢓꢃ &ꢃ ꢉꢁꢊꢇꢆꢏꢃ +ꢃ ꢆꢊꢐꢋꢏꢃꢃ
&Oꢃꢀꢊꢀꢒꢏꢃ1ꢃꢂꢀꢊꢄꢀꢊꢃ
ꢂꢁ&KORURꢁꢆꢁHWK\OꢁꢈꢁSURS\Oꢁꢆ+ꢁS\UD]ROH ꢉ;9,,ꢊꢃꢃ
(WK\OK\GUD]LQHꢅꢃ ꢁꢊꢄꢃ Jꢃ ꢌꢁꢊꢁꢂꢃ PROꢍꢅꢃ DQGꢃ WULHWK\ODPLQHꢅꢃ
ꢂꢊꢁꢂꢃJꢃꢌꢁꢊꢁꢂꢃPROꢍꢅꢃZHUHꢃDGGHGꢃGURSZLVHꢃXQGHUꢃVWLUULQJꢃ
WRꢃDꢃVROXWLRQꢃRIꢃꢂꢊꢄꢒꢃJꢃꢌꢁꢊꢁꢂꢃPROꢍꢃRIꢃꢂꢅꢆꢈGLFKORURYLQ\Oꢃ
SURS\Oꢃ NHWRQHꢃ LQꢃ ꢋꢁꢃ P Oꢃ RIꢃ GLHWK\Oꢃ HWKHUꢊꢃ7KHꢃ P L[WXUHꢃ
ZDVꢃ VWLUUHGꢃ IRUꢃ ꢂꢃ Kꢅꢃ WKHꢃ SUHFLSLWDWHꢃ RIꢃ WULHWK\ODPLQHꢃ
K\GURFKORULGHꢃZDVꢃILOWHUHGꢃRIIꢅꢃWKHꢃILOWUDWHꢃZDVꢃHYDSRꢈ
UDWHGꢅꢃ DQGꢃ WKHꢃ UHVLGXHꢃ ZDVꢃ GLVWLOOHGꢃ XQGHUꢃ UHGXFHGꢃ
SUHVVXUHꢊꢃ<LHOGꢃꢂꢊꢆꢀꢃJꢃꢌꢒꢇ#ꢍꢅꢃESꢃꢒꢁƒ&ꢃꢌꢇꢃPPꢍꢅꢃ Q ꢃ ꢃ
ꢂꢊꢉꢐꢋꢐꢊꢃ,5ꢃVSHFWUXPꢅꢃ ꢅꢃFP ꢓꢃꢋꢂꢉꢁꢅꢃꢋꢂꢆꢁꢃꢌ &±+ꢍꢏꢃ
ꢂꢁ&KORURꢁꢆꢁKHSW\OꢁꢈꢁSURS\Oꢁꢆ+ꢁS\UD]ROH ꢉ;9,,,ꢊꢃ
ZDVꢃ V\QWKHVL]HGꢃ DVꢃ GHVFULEHGꢃ DERYHꢃ IRUꢃ FRP SRXQGꢃ
;9,,ꢃIURPꢃꢂꢊꢋꢃJꢃꢌꢁꢊꢁꢂꢃPROꢍꢃRIꢃKHSW\OK\GUD]LQHꢅꢃꢂꢊꢁꢂꢃJꢃ
ꢌꢁꢊꢁꢂꢃPROꢍꢃRIꢃWULHWK\ODPLQHꢅꢃDQGꢃꢂꢊꢄꢒꢃJꢃꢌꢁꢊꢁꢂꢃPROꢍꢃRIꢃ
ꢂꢅꢆꢈGLFKORURYLQ\OꢃSURS\OꢃNHWRQHꢊꢃ<LHOGꢃꢆꢊꢋꢆꢃJꢃꢌꢐꢇ#ꢍꢅꢃ
ESꢃꢂꢆꢀƒ&ꢃꢌꢋꢃPPꢍꢅꢃQ ꢃ ꢃꢂꢊꢉꢐꢆꢋꢊꢃ,5ꢃVSHFWUXPꢅꢃ ꢅꢃFP ꢓꢃ
ꢋꢂꢆꢁꢃꢌ &±+ꢍꢏꢃꢆꢀꢇꢁꢅꢃꢆꢀꢆꢁꢅꢃꢆꢐꢇꢁꢃꢌ&±+
ꢍꢏꢃꢂꢄꢁꢁꢃ
ꢌ& 1ꢍꢊꢃ +ꢃ105ꢃVSHFWUXPꢃꢌ&'&O ꢍꢅꢃ ꢅꢃSSPꢓꢃꢒꢊꢆꢄꢃVꢃ
ꢌꢂ+ꢅꢃꢇꢈ+ꢍꢅꢃꢋꢊꢀꢒꢃTꢃꢌꢆ+ꢅꢃ&+ ꢅꢃ-ꢃ ꢃꢒꢊꢂꢃ+]ꢍꢅꢃꢆꢊꢇꢄꢃWꢃꢌꢆ+ꢅꢃ
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