Water → HCID 43686020, compound

HRID 250741Notes

Reaction equation

HRID 250741 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16](F)[CH:15]=1>O1CCCC1>[CH2:1]([NH:5][C:18]1[CH:19]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]=1[N+:20]([O-:22])=[O:21])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 43686020HCID 43686020, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of isobutylamine (14 mL, 0.138 mol), potassium carbonate (10.4 g, 0.075 mol) and water (50 mL) to a solution of 4-chloro-2-fluoro-nitrobenzene (11.0 g, 0.063 mol) in tetrahydrofuran (0.3 L) and stir at ambient temperature for 3 hours. Separate phases and wash organic layer with 1:1 solution of 1N HCl (aq)/saturated sodium chloride. Dry organic phase with solid magnesium sulfate, filter and concentrate under reduced pressure to give 14.5 g (0.063 mol) of the desired compound as an orange oil that solidifies upon standing.

Workup

  1. washSeparate phases and wash organic layer with 1:1 solution of 1N HCl (aq)/saturated sodium chloride
  2. filtrationDry organic phase with solid magnesium sulfate, filter
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7afaa7ed03ce46fbb8aea504a67f7f99
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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