Phosphorus oxychloride → 8-(Benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 989396Notes

Reaction equation

HRID 989396 reaction equation
[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[NH:18][CH:17]=[C:16]([C:21]#[N:22])[C:15]3=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:30])=O>>[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[N:18]=[CH:17][C:16]([C:21]#[N:22])=[C:15]3[Cl:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 117726788-Benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 219564648-(Benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrileYield 97.9%

Procedure

A mixture of 8-benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (11.4 g, 31.9 mmol) and phosphorus oxychloride (147 g, 959 mmol) is heated under reflux for one hour. After cooling to room temperature, the reaction mixture is evaporated under vacuum to remove the volatiles. The residue is carefully slurried in cold saturated aqueous sodium bicarbonate solution (500 mL). The solids are collected by filtration, washed thoroughly with saturated aqueous sodium bicarbonate solution and water and dried to give 11.7 grams of crude 8-(benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile as a light orange solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for one hour
  3. customthe reaction mixture is evaporated under vacuum
  4. customto remove the volatiles
  5. filtrationThe solids are collected by filtration
  6. washwashed thoroughly with saturated aqueous sodium bicarbonate solution and water
  7. customdried

Sources & evidence

ORD record
ord-93dde6f573c643f2b2a6c7f6e713d0d2
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

Loading…