Nitric Acid → 2-(2-Fluorophenyl)-1,5-dimethyl-4-nitro-1H-pyrazol-3(2H)-one

HRID 1478825Notes

Reaction equation

HRID 1478825 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH:11]=[C:10]([CH3:14])[N:9]1[CH3:15].[N+:16]([O-])([OH:18])=[O:17].O.CC(OC)(C)C>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([CH3:14])[N:9]1[CH3:15]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 15413tert-Butyl methyl etherHCID 686785242-(2-Fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one

Product 1

HCID 1185132912-(2-Fluorophenyl)-1,5-dimethyl-4-nitro-1H-pyrazol-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(2-Fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (260 g, 1261 mmol) in TFA (1040 ml) was cooled to −10° C. and stirred for 30 mins. To the mixture was added fuming nitric acid (84 ml) dropwise and this was stirred for 15 mins under cooling then at RT for 1 hr. The resulting mixture was poured onto a mixture of ice (1500 ml), water (1000 ml) and TBME (2500 ml) and stirred until the ice melted, then at RT for 1 hr. The mixture was filtered, washed with water (200 ml) and TBME (1000 ml). The collected crystals were dried to give the title compound as red-brown crystals.

Workup

  1. stirringthis was stirred for 15 mins
  2. temperatureunder cooling
  3. waitat RT for 1 hr
  4. waitat RT for 1 hr
  5. filtrationThe mixture was filtered
  6. washwashed with water (200 ml) and TBME (1000 ml)
  7. customThe collected crystals were dried

Sources & evidence

ORD record
ord-36fc80673fa44781a1a4294759cefda4
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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