Hydrochloric Acid → HCID 67459927, compound

HRID 1824699Notes

Reaction equation

HRID 1824699 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)[NH2:5].Cl.[N:21]([O-:23])=[O:22].[Na+].[N+:25]([CH2:28][CH2:29][CH3:30])([O-])=O.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][N:25]=[C:28]([N+:21]([O-:23])=[O:22])[CH2:29][CH3:30])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79031-NitropropaneHCID 14798Sodium HydroxideHCID 22142156HCID 22142156, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 67459927HCID 67459927, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 3-fluoro-4-[3-(trifluoromethyl)phenoxy]aniline (1.35 g) prepared as described in Step 2 of Example 1, water (18.2 mL), and conc. HCl (1.5 mL) was stirred overnight at room temperature. The suspension mixture was cooled to −5° C. and was added dropwise of NaNO2 (0.36 g in 2 mL water) over a period of about 10 min. The reaction mixture was further stirred for 30 minutes, and added CH3CO2Na3H2O (6.6 g). The resulting salt was added to a previously prepared solution of nitropropane (0.44 g) and NaOH (0.20 g) in ethanol (8 mL) and water (2 mL). The resulting mixture was stirred at 0° C. and then at room temperature overnight. It was filtered to give a red solid that was subsequently purified by column chromatography on silica (40% dichloromethane/hexane).

Workup

  1. customprepared
  2. temperatureThe suspension mixture was cooled to −5° C.
  3. stirringThe reaction mixture was further stirred for 30 minutes
  4. additionadded CH3CO2Na3H2O (6.6 g)
  5. stirringThe resulting mixture was stirred at 0° C.
  6. customat room temperature
  7. customovernight
  8. filtrationIt was filtered
  9. customto give a red solid that
  10. customwas subsequently purified by column chromatography on silica (40% dichloromethane/hexane)

Sources & evidence

ORD record
ord-8ad760c7d5de40e89b93575fc2716853
Source dataset
uspto-grants-2006_05
Patent number
US07045512B2

Reaction notes

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