Phosphorus oxychloride → 4-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile

HRID 2213803Notes

Reaction equation

HRID 2213803 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[CH:20][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:7]=2[CH:6]=1)[NH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]3=O.N1C2C(=CC=CC=2)C=C(C#N)C=1.P(Cl)(Cl)([Cl:38])=O>CN(C)C=O>[Cl:38][C:11]1[C:10]2[C:15](=[CH:16][C:7]3[CH:6]=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[C:21]([O:22][CH3:23])=[CH:20][C:8]=3[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 931773-QuinolinecarbonitrileHCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 115157734-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 1.11 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo]quinoline-3-carbonitrile (1:1 mixture) and 5 mL of phosphorus oxychloride is added 0.15 mL of anhydrous dimethylformamide. This is stirred and heated to reflux for 20 minutes using an oil bath, followed concentration in vacuo. The dark residue is quenched with 30 mL of cold water. The solid formed is collected, washed with water and dried to give 1.02 g (87%) of 4-chloro-7-methoxy-8(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-chloro-8-methoxy-7(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture) as a greenish yellow solid, m.p. 195–209° C. dec.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 minutes
  3. concentrationconcentration in vacuo
  4. customThe dark residue is quenched with 30 mL of cold water
  5. customThe solid formed
  6. customis collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5d87c812e7f841959505e28c6e32faaa
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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