Sodium Hydroxide → 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)aniline

HRID 1183911Notes

Reaction equation

HRID 1183911 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:10]=[C:11]([NH:23]C(=O)C)[CH:12]=[CH:13][C:14]=2[O:15][CH2:16][C:17]([CH3:22])([N+:19]([O-:21])=[O:20])[CH3:18])=[CH:7][CH:6]=[N:5]1>O.CO>[CH3:3][N:4]1[C:8]([C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=2[O:15][CH2:16][C:17]([CH3:22])([N+:19]([O-:21])=[O:20])[CH3:18])[NH2:23])=[CH:7][CH:6]=[N:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67265394HCID 67265394, compound

Product 1

HCID 672657453-(2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)anilineYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A solution of sodium hydroxide (70 mg, 1.74 mmol) in water (0.15 mL) was added to a suspension of N-(3-(2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)phenyl)acetamide (84 mg, 0.29 mmol) in methanol (1 mL) and the mixture was stirred at 140° C. in a screw capped vial for 90 min. The mixture was allowed to cool to room temperature, and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and water, the organic layer was dried with sodium sulfate, filtered and evaporated to dryness to afford the title compound (62 mg, 0.21 mmol, 74%) as a yellow oil which was used without further purification. LCMS m/z (%)=291.3 (M+H 98%).

Workup

  1. customcapped vial for 90 min
  2. temperatureto cool to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between dichloromethane and water
  5. dry with materialthe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-992bbd7e09bc4719a31d59956c829e62
Source dataset
uspto-grants-2014_03
Patent number
US08664258B2

Reaction notes

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