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

HRID 989358Notes

Reaction equation

HRID 989358 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.[Cl:24]CCOC1C(OC)=CC2C=C3C(C(=O)C(C#N)=CN3)=CC=2C=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[Cl:24][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 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrileHCID 116384657-(2-Chloroethoxy)-8-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[g]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-f4d69c700e514154887c632f90bab6da
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

Loading…