Water → (5-Chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amine

HRID 250748Notes

Reaction equation

HRID 250748 reaction equation
[NH2:1][C@@H:2]([C:4]([CH3:7])([CH3:6])[CH3:5])[CH3:3].C(=O)([O-])[O-].[K+].[K+].O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18](F)[CH:17]=1>C1COCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[C:20]([NH:1][C@H:2]([CH3:3])[C:4]([CH3:7])([CH3:6])[CH3:5])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 5324845(R)-3,3-Dimethyl-2-aminobutane

Product 1

HCID 66869060(5-Chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amineYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Add 2-(R)-amino-3,3-dimethylbutane (20 mL, 0.148 mol), potassium carbonate (14.3 g, 0.104 mol) and water (50 mL) to a solution of 4-chloro-2-fluoronitrobenzene (13.3 g, 0.076 mol) in THF (450 mL) and stir at 75° C. for 3 h Cool to ambient temperature. Concentrate to ½ volume, dilute with ethyl acetate and wash with 1N HCl (4×100 mL), water, saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate and concentrate to give the title compound as an orange solid (19.6 g, quant).

Workup

  1. temperatureCool to ambient temperature
  2. concentrationConcentrate
  3. additiondilute with ethyl acetate
  4. washwash with 1N HCl (4×100 mL), water, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdry with magnesium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-9f13736c3cc0452799f7c738cd081826
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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