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

HRID 902420Notes

Reaction equation

HRID 902420 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, is 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. washis washed with cold water
  9. customdried

Sources & evidence

ORD record
ord-b1a17692c7414965bf2081561901fab0
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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