6-Bromoquinoline → Quinoline-6-carbonitrile

HRID 333987Notes

Reaction equation

HRID 333987 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12]([Cu])#[N:13]>N1C=CC=CC=1>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 792436-BromoquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 592995Quinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of 6-bromoquinoline (2.0 g, 9.61 mmol) in pyridine (30 mL) was added CuCN (3.0 g, 33.6 mmol) at RT under inert atmosphere. The reaction mixture was gradually heated to 200° C. and stirred for 8 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT, diluted with ice-cold H2O (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography (eluting with 30% EtOAc/hexane) afforded compound I-C (1.25 g, 8.0 mmol, 83%) as white solid. 1H NMR (200 MHz, CDCl3): δ 9.08-9.05 (m, 1H), 8.25-8.19 (m, 3H), 7.86 (dd, J=8.6, 1.8 Hz, 1H), 7.55 (dd, J=8.6, 1.8 Hz, 1H). MS (ESI): 155 [M+H]+.

Workup

  1. customAfter complete consumption of the starting material (by TLC)
  2. temperaturethe reaction mixture was cooled to RT
  3. additiondiluted with ice-cold H2O (100 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic extracts were washed with H2O (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8be3fcc2bcef4916b0310e101b56d938
Source dataset
uspto-grants-2014_11
Patent number
US08883797B2

Reaction notes

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