Phosphorus oxychloride → 2-Chloro-5,6,7,8-tetrahydroquinoline-3-carbonitrile

HRID 577792Notes

Reaction equation

HRID 577792 reaction equation
O=[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[NH:3]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27682602-Oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Product 1

HCID 37798182-Chloro-5,6,7,8-tetrahydroquinoline-3-carbonitrileYield 75%

Procedure

To 2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (6.0 g, 34.4 mmol) was added phosphorus oxychloride (20 mL), this mixture was stirred at RT for 1 h, and then refluxed for 12 h. Excess phosphorous oxychloride was distilled off, and the residue was poured into ice cooled water. The aqueous solution was basified with saturated sodium bicarbonate solution, and the precipitate that formed was filtered off. The precipitate was purified by column chromatography eluting with 2% ethyl acetate and petroleum ether to afford 2-chloro-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (5.00 g), yield: 75%.

Workup

  1. temperaturerefluxed for 12 h
  2. distillationExcess phosphorous oxychloride was distilled off
  3. additionthe residue was poured into ice
  4. temperaturecooled water
  5. customthe precipitate that formed
  6. filtrationwas filtered off
  7. customThe precipitate was purified by column chromatography
  8. washeluting with 2% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-2970124c484046d98e9b3215ced3ca45
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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