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

HRID 2213823Notes

Reaction equation

HRID 2213823 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:5][C:6]2[CH:15]=[C:14]3[C:9]([C:10](=O)[C:11]([C:16]#[N:17])=[CH:12][NH:13]3)=[CH:8][C:7]=2[CH:19]=1.P(Cl)(Cl)([Cl:31])=O>C1(C)C=CC=CC=1>[Cl:31][C:10]1[C:9]2[C:14](=[CH:15][C:6]3[CH:5]=[C:4]([O:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:3]([O:2][CH3:1])=[CH:19][C:7]=3[CH:8]=2)[N:13]=[CH:12][C:11]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 120627417-Methoxy-8-(2-morpholin-4-yl-ethoxy)4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 120627424-Chloro-7-methoxy-8-(2-morpholin-4-yl ethoxy)benzo[g]quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 2.32 g (6.11 mmol) of 7-methoxy-8-(2-morpholin-4-yl-ethoxy)-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 35 mL of phosphorus oxychloride is heated under reflux for 1 hour, then cooled to room temperature. Excess phosphorus oxychloride is evaporated to yield a residue, to which toluene is added and the resulting solution is reduced in vacuo. Toluene is added and evaporated twice more. The resulting residue is cooled with ice bath, neutralized with cold saturated solution of sodium bicarbonate and stirred. The solid is collected by filtration, washed with cold water and dried to yield 1.989 g of 4-chloro-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile as a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. customExcess phosphorus oxychloride is evaporated
  4. customto yield a residue
  5. customevaporated twice more
  6. temperatureThe resulting residue is cooled with ice bath
  7. filtrationThe solid is collected by filtration
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-25f5aa142caf43fabe5038175c71753b
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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