Phosphorus oxychloride → HCID 178486400, compound

HRID 989375Notes

Reaction equation

HRID 989375 reaction equation
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[CH:3]=1)[NH:11][CH:10]=[C:9]([C:14]#[N:15])[C:8]3=O.P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:8]1[C:7]2[C:12](=[CH:13][C:4]3[CH:3]=[C:2]([OH:1])[C:18]([O:19][CH3:20])=[CH:17][C:5]=3[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486405HCID 178486405, compound

Product 1

HCID 178486400HCID 178486400, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 3.0 g (11.3mmol) of 8-hydroxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 20.0 mL of phosphorus oxychloride is heated under reflux for 0.5 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 2.83 g of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid. A sample of the material is purified by silica gel chromatography, eluting with 97:3 methylene chloride/methanol to yield a yellow solid, mp. >300° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 0.5 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-43f31f00fdef424c8e5910d8419cf549
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

Loading…