Dimethylformamide → 1,2,3,4-Tetrahydroquinoline-6-carbonitrile

HRID 1520153Notes

Reaction equation

HRID 1520153 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[CH3:12][N:13](C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:8]1[C:9]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 146654131,2,3,4-Tetrahydroquinoline-6-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

To a solution of 6-bromo-1,2,3,4-tetrahydroquinoline (10 g, 47.15 mmol) in N,N-dimethylformamide (80 mL) was added Pd(PPh3)4 (2.8 g, 2.42 mmol), and zincdicarbonitrile (6.4 g, 54.49 mmol) and the reaction was stirred for 2 h at 120° C. in an oil bath. The reaction was quenched by the addition of water (400 mL) and extracted with dichloromethane (3×50 mL), and concentrated in vacuo to give a residue, which was purified by a silica gel chromatography with 1%-20% ethyl acetate in petroleum ether to give 1,2,3,4-tetrahydroquinoline-6-carbonitrile as a yellow solid (6 g, 80%).

Workup

  1. customThe reaction was quenched by the addition of water (400 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by a silica gel chromatography with 1%-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-619caa6af6fd4a0b95dc7e6c95696e59
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…