Nitric Acid → HCID 22184680, compound

HRID 1061546Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[CH:17]=[C:13]2[N:12]=[C:11]([CH3:20])[N:10]=1.[N+:21]([O-])([OH:23])=[O:22].CCOC(C)=O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[C:17]([N+:21]([O-:23])=[O:22])=[C:13]2[N:12]=[C:11]([CH3:20])[N:10]=1

Participants

Conditions

Temperature: -7.5 °C

Procedure

A solution of 4-(2,4-dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine (653 mg, 2.2 mmol) in acetic anhydride (4 mL) was cooled with stirring to −5 to −10° C. A solution of fuming nitric acid (160 mg, 2.55 mmol) in acetic anhydride (2 mL) was added dropwise over 15 min. The reaction mixture was stirred at the same temperature for 3 h, then it was partitioned between water and ether three times. The combined organic layers were washed with a saturated NaHCO3 solution, dried over MgSO4 and filtered. Solvent was removed in vacuo to provide a solid. Column chromatography (EtOAc:hexanes::1:9 to 1:4) provided a solid (166 mg, 21% yield) after removal of solvent in vacuo: NMR (CDCl3, 300 MHz): δ 7.64 (d, 1H, J=8), 7.63 (d, 1H, J=2), 7.50 (dd, 1H J=8, 2), 3.19 (q, 2H, J=7), 2.94 (s, 3H), 1.32 (t, 3H, J=7).

Workup

stirringThe reaction mixture was stirred at the same temperature for 3 h
customit was partitioned between water and ether three times
washThe combined organic layers were washed with a saturated NaHCO3 solution
dry with materialdried over MgSO4
filtrationfiltered
customSolvent was removed in vacuo
customto provide a solid

Sources & evidence

ORD record: ord-99826a4d50ba4363bb8a3cfdbeb7c0a5
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960583B2

Reaction notes

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