Boron trifluoride etherate → 3-Fluoroquinoline

HRID 2098030Notes

Reaction equation

HRID 2098030 reaction equation
C(ON=O)(C)(C)C.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10](N)[CH:9]=1.B(F)(F)[F:20].CCOCC>C1C(Cl)=CC=C(Cl)C=1>[F:20][C:10]1[CH:9]=[N:8][C:17]2[C:12]([CH:11]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 10906Tert-Butyl nitriteHCID 113753-Aminoquinoline

Product 1

HCID 964053-Fluoroquinoline

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butylnitrite (4.6 ml, 38.7 mmol) was added dropwise over 15 min to a solution of quinolin-3-amine (4.61 g, 32.0 mmol) and borontrifluoride-etherate (6 ml, 47.3 mmol) in dichlorobenzene (100 ml). The solution was heated to 100° C. After stirring for 1 h, the solution was cooled to ambient temperature and the dichlorobenzene was decanted leaving 3-fluoroquinoline as a black residue. Method [8] retention time 3.28 min by HPLC (M+ 148).

Workup

  1. temperaturethe solution was cooled to ambient temperature
  2. customthe dichlorobenzene was decanted

Sources & evidence

ORD record
ord-8eed76372bb54e98bbf189045894b89d
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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