Phosphorus trichloride → HCID 22466634, compound

HRID 612178Notes

Reaction equation

HRID 612178 reaction equation
P(Cl)(Cl)[Cl:2].O[CH2:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:28]#[N:29])[CH:10]=[CH:11][CH:12]=1>CN(C=O)C>[Cl:2][CH2:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:28]#[N:29])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 9923792HCID 9923792, compound

Product 1

HCID 22466634HCID 22466634, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To 14 ml of DMF was added phosphorous trichloride (0.70 ml, 8.0 mmol) with stirring at 25-30° C. After 60 m, the mixture was cooled to 0° C., and a suspension of 4-[3-(hydroxymethyl)phenylamino]-6,7-dimethoxy-3-quinolinecarbonitrile (1.34 g, 4.0 mmol) in 6 ml of DMF was added. The mixture was warmed to 25° C., stirred 15 m, recooled in ice bath, and partitioned with methylene chloride-aqueous sodium bicarbonate. The organic layer was washed with water, dried, and concentrated to give 1.15 g of an amber solid; NMR (CDCl3) δ 4.79(s, CH2Cl).

Workup

  1. temperatureAfter 60 m, the mixture was cooled to 0° C.
  2. additionwas added
  3. temperatureThe mixture was warmed to 25° C.
  4. stirringstirred 15 m
  5. custompartitioned with methylene chloride-aqueous sodium bicarbonate
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-48d0d5f9972b4a479977ca09b82f01fe
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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