Phosphorus oxychloride → HCID 19094040, compound

HRID 487123Notes

Reaction equation

HRID 487123 reaction equation
O[C:2]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516498HCID 178516498, compound

Product 1

HCID 19094040HCID 19094040, compoundYield 85.9%

Procedure

To 0.6 g of 2-hydroxy-N-(2-phenylethyl)-4-quinolinamine was added 15 mL of POCl3. The mixture was heated to reflux overnight, then cooled and concentrated to dryness. A mixture of ammonium hydroxide in water was added, then the product was extracted into CH2Cl2. This solution was concentrated to dryness, and the product was recrystallized from pentane/CH2Cl2, giving 0.55 g of the title product. Yield 85.9%. M.P. 132°-133° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated to dryness
  5. additionA mixture of ammonium hydroxide in water
  6. additionwas added
  7. extractionthe product was extracted into CH2Cl2
  8. concentrationThis solution was concentrated to dryness
  9. customthe product was recrystallized from pentane/CH2Cl2

Sources & evidence

ORD record
ord-29c1b8d487fc46b5ac72002870a9fb0c
Source dataset
uspto-grants-1994_03
Patent number
US05294622

Reaction notes

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