5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-2-nitro-N-propylbenzenamine → 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-N-propyl-1,2-benzenediamine

HRID 1198412Notes

Reaction equation

HRID 1198412 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:26])=[CH:14][C:15]([N+:23]([O-])=O)=[C:16]([N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[C:15]([NH2:23])=[CH:14][C:13]=2[F:26])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:8])[F:9]

Participants

3

Reactant 1

HCID 152785765-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-2-nitro-N-propylbenzenamine

Product 1

HCID 194367695-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-N-propyl-1,2-benzenediamineYield 81.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.2 g (0.013 mole) 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-2-nitro-N-propylbenzenamine in 100 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 2.2 g (0.039) mole iron powder was added in 3 portions over 5 min. The solution was stirred at 80° C. for an additional 30 min. The solution was cooled and filtered through Celite®. The filtrate was diluted with 100 mL water and extracted three times with ethyl acetate. The ethyl acetate extracts were washed with a saturated NaHCO3 solution, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified chromatographically using 30% ethyl acetate in hexane as the eluent to give 3.85 g (80%) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-N-propyl-1, 2-benzenediamine as a light yellow oil, nD25 1.5352.

Workup

  1. temperatureThe heat
  2. customnitrogen were removed
  3. addition2.2 g (0.039) mole iron powder was added in 3 portions over 5 min
  4. temperatureThe solution was cooled
  5. filtrationfiltered through Celite®
  6. additionThe filtrate was diluted with 100 mL water
  7. extractionextracted three times with ethyl acetate
  8. washThe ethyl acetate extracts were washed with a saturated NaHCO3 solution
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-d01dc579a31140a887406e6d78516a04
Source dataset
uspto-grants-1994_01
Patent number
US05281571

Reaction notes

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