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

HRID 1911762Notes

Reaction equation

HRID 1911762 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. The excess phosphorous oxychloride was distilled off, and the residue was poured into ice-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. distillationThe excess phosphorous oxychloride was distilled off
  3. additionthe residue was poured into ice-water
  4. customthe precipitate that formed
  5. filtrationwas filtered off
  6. customThe precipitate was purified by column chromatography
  7. washeluting with 2% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-799169fda5c9450b87220763bb66f63f
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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