Hydrochloric Acid → (2-Aminophenyl)(5-fluoropyridin-2-yl)methanone

HRID 746738Notes

Reaction equation

HRID 746738 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#N.[Li]CCCC.Cl.[OH-:24].[Na+]>C1(C)C=CC=CC=1>[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1)=[O:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 729132-AminobenzonitrileHCID 27831712-Bromo-5-fluoropyridineHCID 178418339Butyllithium

Product 1

HCID 69308604(2-Aminophenyl)(5-fluoropyridin-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-30 °C

Procedure

2-Bromo-5-fluoropyridine (10 g, 56.8 mmol) and 2-aminobenzonitrile (5.6 g, 47.4 mmol) were dissolved in 100 mL of toluene and cooled to −30° C. To the resulting solution was added nBuLi (1.6 M in hexanes, 65 mL, 104 mmol, 2.2 equv) dropwise, and the reaction mixture was warmed to 0 deg for 90 minutes. The reaction mixture was then poured into 100 mL of cooled 3N HCl and stirred for 15 minutes, then 5N NaOH was added until the reaction mixture turned basic. The reaction mixture was extracted with CH2Cl2 (3×100 ml), washed with brine (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (0% to 30% EtOAc/hexanes) gave the title compound as a solid (LC/MS found: 217.2)

Workup

  1. temperaturethe reaction mixture was warmed to 0 deg for 90 minutes
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×100 ml)
  3. washwashed with brine (1×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90c492fc0c5d4ef8a47a1dae17a55e6a
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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