N,N-Diethylaniline → 2-Chloro-5,6,7,8-tetrahydroquinoline

HRID 2270431Notes

Reaction equation

HRID 2270431 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178515716HCID 178515716, compound

Product 1

HCID 131692632-Chloro-5,6,7,8-tetrahydroquinoline

Procedure

A solution of 0.7 g of 2-hydroxy-5,6,7,8-tetrahydroquinoline (prepared according to the methods outlined by Meyers et al., J. Org. Chem., 29: 1435-1438, 1964) and 0.1 g of diethylaniline in 7 mL of phosphorus oxychloride is refluxed for 2 h, cooled and concentrated. The residue taken is up in chloroform, washed with excess 3 N NaOH solution and the organic layer dried and concentrated to provide crude 2-chloro-5,6,7,8-tetrahydro-quinoline (0.45 g) as an oil.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. washwashed with excess 3 N NaOH solution
  4. customthe organic layer dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5bde9d82654d4fa7b1b08660c69413df
Source dataset
uspto-grants-2001_12
Patent number
US06331629B1

Reaction notes

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