Phosphorus oxychloride → 4-Chloroquinoline-8-carbonitrile

HRID 2060892Notes

Reaction equation

HRID 2060892 reaction equation
O=[C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[CH:3]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 147925984-Oxo-1,4-dihydroquinoline-8-carbonitrile

Product 1

HCID 147925994-Chloroquinoline-8-carbonitrile

Procedure

4-Oxo-1,4-dihydroquinoline-8-carbonitrile (0.40 g, 0.24 mmol, WO2004/113303) and phosphorous oxychloride (10 mL) were heated to 100° C. for 1.5 h. Solvent removed in vacuo. EtOAc (50 mL) was added and organic phase washed with sat. aqueous Na2CO3 solution, brine (20 mL) and dried (MgSO4). Solvent removed in vacuo to give the title compound: RT=3.09 min; m/z (ES+)=189.0 [M+H]+.

Workup

  1. customSolvent removed in vacuo
  2. additionEtOAc (50 mL) was added
  3. washorganic phase washed with sat. aqueous Na2CO3 solution, brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent removed in vacuo

Sources & evidence

ORD record
ord-43ccf59701574dd599a496da65d5fe42
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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