Ammonium Hydroxide → HCID 59191360, compound

HRID 626025Notes

Reaction equation

HRID 626025 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11](N)=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2].N([O-])=[O:21].[Na+].C([O-])(O)=O.[Na+].[NH4+].[OH-]>OS(O)(=O)=O.O.S([O-])([O-])(=O)=O.[Cu+2].[Cu-]=O>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11]([OH:21])=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2]

Participants

9

Reactant 4

HCID 14923Ammonium HydroxideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 59191245HCID 59191245, compound

Product 1

HCID 59191360HCID 59191360, compoundYield 39%

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-ethyl-2-methoxyphenoxy)-3-fluoroaniline (215 mg; 0.82 mmol) in H2SO4 35%, at 0° C., was added a solution of NaNO2 (69 mg; 1 mmol) in water (1 mL). The mixture was stirred 30 min. at 0° C. A solution of copper(II) sulphate (1.85 g; 11.6 mmol) in 6 mL of water was added, followed by copper(I) oxide (99 mg; 0.69 mmol). The reaction was stirred 45 min. at room temperature, then hydrolysed with NaHCO3 sat (6 mL) and NH4OH. The mixture was extracted with ethyl acetate (3*5 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (85 mg; 0.032 mmol; 39%) was obtained as an oil, after purification by preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. stirringThe reaction was stirred 45 min. at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (3*5 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13a947c359e5462ab683c88817b152ef
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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